Agent for fighting against undesirable plants
Abstract
Benzenesulfonyl isocyanates of the general formula <CHEM> wherein R is alkyl, alkenyl, cycloalkyl, cycloalkenyl or cycloalkylalkyl, any of which may be substituted; R2 is H, halogen, alkyl, -NO2, -OCH3, -SCH3, CF3, SO2CH3, N(CH3)2, CN; R3 is H, Cl, Br or CH3; are valuable intermediates for the production of N-(heterocyclicaminocarbonyl)arylsulfonamides having herbicidal and plant growth regulant activities. The novel compounds (I) can be made by reacting the corresponding sulfonamide with phosgene.

Term
Term ended
Expired 29 May 1994, 32.3 years ago.
- Priority
- Filed
- Granted
- Expired
- Today
29 claims: 3 independent, 26 dependent
- 1Zastrzeżenia patentowe 1. Środek do zwalczania niepożądanej roślinności, zawierający substancję czynną w połączeniu ze 6tałym lub ciekłym rozcieńczalnikiem i/lub substancją powierzchniowo-czynną, znamienny tym, że jako substancję czynną zawiera nowy związek o ogólnym wzorze 1, w którym Q oznacza atom tlenu, R oznacza rodnik alkilowy o 1—12 atomach węgla, rodnik alkilowy o 2—6 atomach węgla zawierający 1—4 podstawników, z których najwyżej 3 oznaczają atomy fluoru, chloru albo bromu, najwyżej 2 oznaczają grupy metoksylowe i najwyżej 1 oznacza grupę cyjanową, albo R oznacza rodnik alkenylowy o 3—10 atomach węgla, rodnik alkenylowy o 3—6 atomach węgla podstawiony 1—3 atomami fluoru, chloru albo bromu, albo R oznacza grupę —CH 2 CN, —CI^COgCHj, —CH 2 CO 2 C 2 H 5 , rodnik cykloalkilowy o 5—8 atomach węgla, rodnik cykloalkilowy o 5—6 atomach węgla podstawiony 1—4 rodnikami metylowymi, metoksylowymi, alkilowymi o 2—4 atomach węgla lub atomami fluoru, chloru albo bromu, lub też rodnik cykloalkenylowy o 5—8 atomach węgla, rodnik cykloalkiloalkilowy o 4—10 atomach węgla, rodnik cykloalkiloalkilowy o 4r—8 atomach węgla podsta66 wiony 1 lub 2 rodnikami [metylowymi, rodnik dwucykloalkenylowy o 7—10 atomach węgla, rodnik trójcykloalkilowy o 10 atomach węgla, rodnik trójcykloalkenylowy o 10 atomach węgla, rodnik dwucykloalkilowy o 7—10 htomach węgla, grupę o wzorze 10, w którym Rg oznacza rodnik alkilowy o 1—3 atomach węgla lub, atom wodoru, a Rio i Rn są jednakowe albo różne i oznaczają atomy wodoru, rodniki alkilowe o 1—3 atomach węgla, atomy chloru lub bromu, grupy —OCH r lub —OC2H5, albo Rio i Rn razem oznaczają pięciolub sześcioczłonowy pierścień o wzorze ll lub 12, a n we wzorze 10 oznacza liczbę zero, 1, 2 lub 3, przy czym całkowita liczba atomów węgla wynosi najwyżej 12, albo też R oznacza grupę o wzorze 13, 14, 15, 16, 17, 18, OS0, 20 lub 21, przy czym we wzorze 14 A oznacza atom tlenu lub siarki i Αχ we wzorach 13, 17, 18, 20 i 21 oznacza atom tlenu lub siarki albo grupę SO 2 , ponadto R oznacza atom wodoru, atom metalu alkalicznego oznaczony literą M. albo grupę o wzorze —CHaCHjORj, —CHjCHjCHaORr lub —CH/CHg/CH 2 OR 7 , w których to wzorach R 7 oznacza rodnik —CHjCHj, —CH/CH3/2, rodnik fenylowy, rodnik —CH 2 CH 2 C1 albo —CH 2 CC1j, lub też R oznacza grupę o wzorze -^/CH 2 CH2O/ n ,R 8 lub [CH/CHg/CHjOJ n ,R 8 , w których to wzorach Rg oznacza grupę —CH>, —€H 2 CH 8 , —CH/CHj/j, grupę fenylową, grupę —CH 2 CH 2 C1 lub —CH 2 CC1 8 , a n' oznacza liczbę 2 aUbo 3, tuzy czym R zawiera razem najwyżej 13 atomów węgla, albo też R oznacza grupę o wzorze 22 lub 23, w których to wzorach R^ oznacza rodnik —CHj, —CH 2 CH$, —CH/CHj/j lub rodnik fenylowy, Rj we wzorze 1 oznacza grupę o wzorze 28 lub 30, przy czym we wzorach 20 i 30 Xj oznacza atom wodoru lub chloru, grupę —OCH 8 , —OCHjCHj lub —CH 8 i Yj oznacza atom wodoru, grupę —CCH> lub —CH 8 , ale Χχ i Υχ równocześnie nie oznaczają atomów wodoru i gdy R x oznacza grupę o wzorze 29 lub 30, wówczas R4 i R$ we wzorze 1 oznaczają atomy wodoru i R zawiera mniej niż 6 atomów węgla;we wzorze 28 X oznacza atom wodoru albo chloru, grupę —CH 8 , —OCH S , —OCHjCHj lub — OCHaCHjOCHj, a Y oznacza atom wodoru ltfb chloru, rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o l—4 atomach Węgla podstawiony grupą —OCHj lub -^OC 2 H 5 albo 1—3 atomami fluoru, chloru lub bromu, lub grupę —CN, —CO 2 CH 8 albo —CO2C2H5, lub też Y oznacza rodnik alkenylowy o 3—4 atomach węgla lub grupę o wzorze —CH 2 C=CR 18 , w którym Ri 8 oznacza atom wodoru, grupę —CH 8 lub —CHjCl, albo Y oznacza grupę o wzorze Αχ—/alkil o 1—3 atomach węgla/, w którym n', A i Αχ mają wyżej podane znaczenie, albo Y oznacza grupę o wzorze —A—CH2C/O/—L, —A—CH/CHg/C/O/—L lub —ACH 2 CH 2 C/O/ l -^L, w których to wzorach L oznacza grupę —NH 2 , grupę o wzorze 31, grupę —NH/ /alkil o 1—4 atomach węgla/, grupę —N/alkil o 1—4 atomach węgla/ 2 Ιτφ grupę alkoksylową o 1—6 atomach węgla, a A ma wyżej podane znaczenie, albo Y oznacza grupę —SON—, —Nj, grupę o wzorze NRx 8 Rx 7 , w którym Rx 8 oznacza atom wodoru lub grupę metylową, a Ri 7 oznacza atom wodoru, rodnik metoksylowy, rodnik alkilowy o 126 541 1—4 atomach węgla, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą —CN, grupą —CO2CH3 lub —CO2C2H5 lub R17 oznacza rodnik alkilowy o 2—3 atomach węgla podstawiony rodnikiem —OCH 5 lub —OC 2 H 5 , albo R17 oznacza rodnik alkenylowy o 3—4 atomach węgla, lub też Rl· i R17 razem oznaczają grupę—CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 —OCH 2 CH 2 albo Y oznacza grupę o wzorze —ORh, w którym Rj/ 2 , —NH 2 albo —CN, R s octnacza atom wodoru, chloru, bromu lub fluoru, albo grupę —CH3, R< oznacza atom wodoru lub grupę —CH3, R 5 oznacza atom wodoru, grupę —CH3 lub —OCH3, a W oznacza atom tlenu lub siarki.
- 2Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetylopdrymidyny lo-2/^aminokarbony lo] -2-metoksykarbonylobenzetnosulfonamid.
- 3Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N[/4,6-dwumetylo-l^,5-triazynylo-2/-aminokarbonyk)] -2-metoksykarbonylobenzenosulfonamid.
- 4Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6nmetylopóryinidynylo-2/-aminokarbonylo]-2-metoksykarfoonylobenzenosulfonamid.
- 5Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-metylo-l,3,5-triazynylo-21-aminokarboinylo]-2-metotksykarbonylobenzenosulfonamid.
- 6Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetoksypirynridynylo-2/-aminokąrbcnylo]-2-metoksykarbonyk>benzenosulfonamid.
- 7Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetoksy-l,3,5,-triazynylo-2/-amiinokarbonylo]-2-metoksykairhonyloibenzenosulfoaiaimid.
- 8Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-i[/4,6-dwumetoksy-l,3,5-triazynylo-2]-amin0karlbonylo]-2-/izoproipoksykarbonylo/benzenosulfonamid.
- 9Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-668 -metyto-l,3,5-triazynylo-2/-aminokarbonylo]-2-/izopropoksykarbonylo/-'benzenosulfonaimid.
- 10Środek według zaistrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetoksy-l,3,5-łriazynylo-2/-aminokarbonylo]-2-/2-chloroetoksykarbonyloż-foenzenosulfonamid.
- 11Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-metylo -1,3,5-trialzynylio-2/-am)inokarbonylo]-2-/2-chloroetoksykarbonyloZ-benzenosulfonamid.
- 12Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-{/4-metoksy-6-metylo-l,3,5-triazynylo-2/-amiinokarbonylo]-2-propoksykarbonylobenzenosulfonamid.
- 13Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6Hmetylopirymidynylo-2/-aminokarbonylo]-2-/2-chloroetoksykarbo,nylo/-benzenosulfonamid.
- 14Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-imetylo-l,3,5-triazynylo-2/-anwinokarbonylo]-2-/2-f eny lo-1 -metyloetoksykarbonyloZ-benzenosulfonamid.
- 15Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-,metylo-l,3,5-triazynylo-2/-amiinokarbonylo] -2-[2-/2-chloroetoksy/-etoksykarbonyto]-benzenosulfonamid.
- 16Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-metylo-l,3,5-triazynylo-2/-aminokarbonylo]-2-/2-etoiksyetoksykarbonylo/-benzenosulfonamid.
- 17Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-rne tyło-1,3,5-triazynylo-2/-aminokar bomy lo]-2.-a lliloksykarbony lobenzeno sulfonamid.
- 18Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-{[4-metylo-6-/l-metoksykarbotnyloetoksy/-pirymidynylo-2]-aminokarbonylo}-2-metoksykarbonylobenzenosulfonamid.
- 19Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-{[4-metylo-6-/l-metoksykarbonyloetoksy/-l,3,5-triazynylo-2]-aiminbkarbonylo} -2-metoksykarbonylobenzenosulfonamid.i
- 20Środek według zastrz. 1, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-metylo-l,3,5-triazynylo-2/-aminokarbonylo]-2-/2-me ty lopropoksykarbohy loZ-benzenosulfonamid.
- 21Środek według zastrz. 1;znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetoksypiryrnidynylo-2/Hairnńiokarbonylo]-2-/alliloksykarbonyloZ-benzenosulfonamid.
- 22Środek do zwalczania niepożądanej roślinności, zawierający substancję czynną w połączeniu ze stałym lub ciekłym rozcieńczalniikiem i/lub substancją powierzchniowo-ozynną, znamienny tym, że jako substancję czynną zawiera nowy związek o ogólnym wzorze 1, w którym Q oznacza atom siarki, R oznacza rodnik alkilowy o 1—12 atomach węgla, rodnik alkilowy o 2—6 atomach węgla zawierający 1—4 podstawników, z których najwyżej 3 oznaczają atomy fluoru, chloru albo bromu, najwyżej 2 oznaczają grupy metoksylowe i najwyżej 1 oznacza grupę cyjanową, albo R oznacza 126 541 rodnik alkeny Iowy o 3—10 atomach węgla, rodnik alkenylowy o 3—6 atomach węgla podstawiony 1—3 atomami fluoru, chloru albo bromu, albo R oznacza grupę —CH 2 CN,—CH 2 CO 2 CHs, —CH 2 CO 2 C 2 Hg, rodnik cykloalkilowy o 5—8 atomach węgla, rodnik cykloalkilowy o 5—8 atomach węgla podstawiony 1—4 rodnikami metylowymi, metoksylowymi, alkilowymi o 2—4 atomach węgla lub atomami fluoru, chloru albo bromu, lub też rodnik cykloalkenylowy o 5—8 atomach węgla, rodnik cykloalkiloalkilowy o 4—10 atomach węgla, rodnik cykloalkiloalkilowy o 4—8 atomach węgla podstawiony 1 lub 2 rodnikami metylowymi, rodnik dwucykloalkenylowy o 7—<10 atomach węgla, rodnik trójcykloalkilowy o 10 atomach węgla, rodnik trójcykloalkenylowy o 10 'atomach węgla, rodnik dwucykloalkilowy o 7—-10 atomach węgla, grupę* o Wzorze 10, w którym R# oznacza rodnik alkilowy o 1—3 atomach węgla lub atom wodoru, a Rio i Rn są jednakowe albo różne i oznaczają atomjP wodoru, rodniki alkilowe o 1—3 atomach węgla, htomy chloru lub bromu, grupy —OCH3 lub —OC2H5, albo Rio i Rn razem oznaczają pięciolub sześcioczłonowy pierścień o wzorze 11 lub 12 a n we wzorze 10 oznacza liczbę zero, 1, 2 lub 3, przy czym całkowita liczba atomów węgla wynosi najwyżej 12, albo też R oznacza grupę o wzorze 13, 44, 15, 16, 17, 18, 19, 20 lub 21, przy czym we wzorze 14 A oznacza atotm tlenu lub siarki i Ai we wzorach 13, 17 ,18, 20 i 21 oznacza atom tlenu lub siarki albo grupę SO 2 , Ri we wzorze 1 oznacza grupę o wzorze 28, 29 lub 30, przy czym we wzorach 29 i 30 Xi oznacza atom wodoru lub chloru, grupę —OCH S , —OCHjCHa lub —CH 3 i Yi oznacza atom wodoru, grupę —ÓCH 3 lub —CH S , ale Xj i Yi równocześnie nie oznaczają atomów wodoru i gdy Ri oznacza grupę o wzorze 29 lub 30, wówczas R< i Rg we wzorze 1 oznaczają atomy wodoru i R zawiera mniej niż 6 atomów węgla;we wzorze 28 X oznacza atom wodoru albo chloru, grupę —CH S , —OCH 3 , —OCH 2 CH 8 lub —OCH 2 CH 2 OCH3, a Y oznacza atom wodoru lub chloru, rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą —OCH3 lub —OC 2 Hg albo li—3 atomami fluoru, chloru lub bromu lub grupą —CN, CO 2 CH 3 , albo —CO 2 C 2 Hg, lub też Y oznacza rodnik alkenylowy o 3—4 atomach węgla lub grupę o wzorze —CH 2 C = CRi3, w którym R13 oznacza atom wodoru, grupę —CH3 lub —CH2C1, albo Y oznacza grupę o wzorze —A—/CH2/n,—Αι/alkil o 1—3 atomach węgla/, w którym n z , A i Aj mają wyżej podane znaczenie, albo Y oznacza grupę o wzorze —A—CH2C/O/—L, —A—CH/CH3/C/O—L lub —ACH 2 CH 2 C/O/—L, w których to wzorach L oznacza grupę —NH 2 , grupę o wzorze 31, grupę —NH/ /alkil o 1—4 atomach węgla/, grupę —N/alkil o 1—4 atomach węgla/ 2 lub grupę alkoksylową o 1—6 atomach węgla, a A ima wyżej podane znaczenie, albo Y oznacza grupę —SCN—, —N 3 , grupę o wzorze NRieRn, w którym Rjg oznacza atom wodoru lub grupę metylową, a R17 oznacza atom wodoru, rodnik metoksylowy, rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—4 atomach podstawiony grupą —CN, grupą —CO 2 CH 2 lub —CO 2 C 2 Hg lub R17 oznacza rodnik alkilowy o 2— 3 atomach węgla podstawiony rodnikiem —OCH 2 lub —OC 2 H«j, albo R17 oznacza rodnik alkenylowy o 3—4 atomach węgla, lub też Rig i R17 razem oznaczają grupę CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 OCH 2 CH 2 albo Y oznacza grupę o wzorze —OR14, w którym Rk oznacza rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 2—4 atomach węgla podstawiony 1—3 atomami fluoru, chloru lub bromu, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą cyjanową, rodnik alkanylowy o 3— 4 atomach węgla lub rodnik o wzorze —CH 2 C=CRi3, w którym R13 ma wyżej podane znaczenie, albo Y oznacza grupę o wzorze 32 lub grupę o wzorze —SR15, w którym Rig oznacza rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—2 atomach węgla podstawiony grupą—CN, albo R15 oznacza rodnik allilowy lub propargilowy, przy czym gdy Y zawiera 4 lub więcej niż 4 atomy węgla, wówczais R zawiera mniej niż 5 atomów węgla, a gdy X oznacza atom chloru, wówcząs i Y oznacza atom chloru i gdy X i Y oznaczają atomy wodoru, wówczas R zawiera mniej niż 5 atomów węgla, Z oznacza grupę =CH lub atom azotu, poza tym, że we wzorze 1 R 2 oznacza atom wodoru, chloru, bromu lub fluoru, rodnik alkilowy o 1—3 atomach węgla, grupę —NOs, —SO 2 CH 8 , —OCH3, —SCH s , —CF$, -^N/CHg/ 2 , —NH 2 albo —CN, R3 oznacza atom wodoru, chloru, bromu, lub fluoru, albo grupę —CH3, R< oznacza atom wodoru lub grupę —CH 8 , Rg oznacza atom wodoru, grupę —CH3, lub —OCH3, a W oznacza atom tlenu lub siarki.
- 23Środek według zastrz. 22, znamienny tym, że jako czynną substancjęzawderaN4/4-metoksy-6Hmetylo-l,3,5-triazynylo-2/-amiinokarbonylo] -2-metylotiokarbonylobenzenosulfonaimad.
- 24Środek według zastrz. 22, znamienny tym, że jako czynną substancję zawiera N-[/4-inetaksy-6-metylo-l,3,5-triazynylo-2/amnnokarbonylo]-2-i20propylotiokarbonylobenzenosulfonamid.
- 25Środek według zastrz. 22, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-8metylopirymidynylo-2-aminokarbonyloJ-2-izopylotiokarbonylobenzenosulfonamid.
- 26Środek do zwalczania niepożądanej roślinności, zawierający substancję czynną w połączeniu ze stałym lub ciekłym rozcieńczalnikiem i/łub substancją powierzchniowo-czynną, znamienny tym, że jako substancję czynną zawiera nowy związek o ogólnym wzorze 1, w którym Q oznacza grupę o wzorze 9, R oznacza atom wodoru, rodnik alkilowy o 1—12 atomach węgla, lub grupę o wzorze /CHsCHaO/n” R12 albo —CH 2 CH 2 CH 2 ORi 2 , w których to wzorach R12 ma wyżej podanej znaczenie, a m w pierwszym z tych wzorów oznacza liczbę 1—3, albo też R oznacza rodnik alkenylowy o 3—10 atomach węgla, rodnik cykloalkilowy o 3— —8 atomach węgla, rodnik cykloalkilowy o 5—8 atomach węgla mający 1—3 podstawników, z których najwyżej 2 stanowią grupy me toksy lowe, a pozostałe stanowią grupy metylowe lub etylowe, albo R oznacza rodnik cykloalkenylowy o 5—6 atomach węgla, rodnik trójfluorometylocyklohaksylowy, rodnik cykloalkiloalkilowy o 4—10 atomach 126 541 węgla, rodnik cykloalkiloalkilowy o 4—8 atomach węgla podstawiony 1 lub 2 rodnikami metylowymi, albo R oznacza grupę —CH 2 CN, —CHjCH 2 CN, grupę o wzorze 24 albo grupę —OCH 3 , grupę —N/CHs/ 2 , grupę o wzorze 10, w którym Rg, Rio, R11 i n mają wyżej podane znaczenie, grupę o wzorze 25 lub 26, grupę o wzorze 27, w którym R' oznacza atom wodoru, rodnik alkilowy o 1—4 atomach węgla, rodnik metoksylowy, aftom fluoru, bromu albo chloru, grupę —CF 3 , —CN, —NO 2 , —SO 2 CH 3 , —SCH 3 albo —N/CH^, R oznacza atom wodoru, rodnik alkilowy o 1—4 atomach węgla, rodnik metoksylowy lub atom fluoru, bromu albo chloru, a R oznacza atom wodoru, rodnik metylowy lub atom chloru, fluoru, albo bromu, Re wie wzorze 9 oznacza atom wodoru, rodnik alkilowy o 1—6 atomach węgla, rodnik allilowy, grupę —CH 2 CN lub —CH 2 CH 2 CN albo R® i R razem oznaczają grupę /CH^, /CH 2 /s, /CH 2 /e, —CH 2 CH 2 OCH 2 CH 2 — albo —CH^H^N/CHg/ /CH 2 CH 2 —, przy czym gdy R oznacza grupę metoksylową, wówczas Re oznacza grupę metylową, a gdy Re oznacza grupę —CH 2 CN lub —CH 2 CH 2 OH, wówczas R oznacza grupę —CH 2 CN lub —CH 2 CH 2 CN, a poza tym R i Re razem zawierają najwyżej 13 atomów węgla, Ri we wzorze 1 oznacza grupę o wzorze 28, 29 lub 30, przy czym we wzorach 29 i 30 Xj oznacza atom wodoru lub chloru, grupę —OCH 3 , —OCH 2 CH S lub —CH S i Yi oznacza atom wodoru, grupę —OCH 3 lub —CH 3 , ale Xi i Yi równocześnie nie oznaczają atomów wodoru i gdy Ri oznacza grupę o wzorze 29 lub 30, wówczas R4 i Rg we wzorze 1 oznaczają atomy wodoru i R zaiwiera mniej niż 6 atomów węgla;we wzorze 28 X oznacza atom wodoru albo chloru, grupę —CH 3 , —OCH 3 , —OCH 2 CH3 lub ^OCHjCHjOCHs, a Y oznacza atom wodoru lub chloru, rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą —OCH 3 lub —CO 2 H 5 albo 1—3 atomami fluoru, chloru lub bromu, lub grupą —CN, —CO 2 CHg albo —CO 2 C 2 H 5 , lub też Y oznacza rodnik alkenylowy o 3—4 atomach węgla lub grupę o wzorze —CH 2 C s CRi 3 , w którym R13 oznacza atom wodoru, grupę —CH 3 lub —CH 2 C1, albo Y, oznacza grupę o wzorze —A—/CH^n’—Ai—/alkil o 1—3 atomach węgla/, w którym ki', A i Aj mają wyżej podane znaczenie, albo Y oznacza grupę o wzorze —A—CH 2 C/O/—L, —A—CH/CH3/C/O/—L, Łub —ACH2CH2C/O/—L, w których to wzorach L oznacza grupę —NH 2 , grupę o wzorze 31, grupę —NH/alkil o 1—4 atomach węgla/, grupę —N/alkil o 1—4 atomach węglaĄ lub grupę alkoksylową o 1—8 atomach węgla, a A ma wyżej podane Znaczenie, albo Y oznacza grupę —SCN—, —N 3 , grupę o wzorze NRi e Ri7, w którym Rje oznacza atom wodoru lub grupę metylową, a R17 oznacza atom wodoru, rodnik metoksylowy, rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą —CN, grupą —CO 2 CH 3 lub —CO 2 C 2 H 5 lub R17 Oznacza rodnik alkilowy o 2—3 atomach węgla podstawiony rodnikiem —OCH 3 lub —OC 2 H5, albo R17 oznacza rodnik alkenylowy o 3—4 atomach węgla, lub też Rie i R17 razem oznaczają grupę —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 OCH 2 CH 2 albo Y oznacza grupę o wzorze —ORj< w którym Rj< oznacza rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 2—4 atomach węgla, podstawiony 1—3 atomami fluoru, chloru lub bromu, rodnik alkilowy o 1—4 atomach węgla podstawiony grupą cyjanową, rodnik alkenylowy o 3—4 atoInach węgla lub rodnik o wzorze —CH 2 C s CRi 3 , w którym R 13 ma wyżej podane znaczenie, albo Y oznacza grupę o wzorze 32 lub grupę o wzorze —SRję w którym R15 oznacza rodnik alkilowy o 1—4 atomach węgla, rodnik alkilowy o 1—2 atomach węgla podstawiony grupą —CN, albo Rjg oznacza rodnik allilowy lub pr opargilowy, przy czym gdy Y zawiera 4 lub więicej niż 4 atomy węgla, wówczas R zawiera mniej niż 5 atomów węgla, a gdy X oznacza atom chloru, wówczas i Y oznacza atom chloru i gdy X i Y oznaczają atomy wodoru, wówczas R zawiera mniej niż 5 atomów węgla, Z oznacza grupę =CH lub atom azotu, poza tym, we wzorze 1 R 2 oznacza atom wodoru, chloru, bromu lub fluoru, rodnik alkilowy o 1—3 atomach węgla, grupę —NO 2 , —SO 2 CH 3 , —OCH 3 , —SGH 3 , —CFg, —N/CH$/ 2 , —NH 2 albo —CN, R3 oznacza atom wodoru, chloru, bromu lub fluoru, albo grupę —CHg, R< oznacza atom wodoru, lub grupę —CHg, Rg oznacza atom wodoru, grupę —CH 3 lub —OCHg, a W oznacza atom tlenu lub siarki.
- 27Środek według zaistrz. 26, znamienny tym, że jako czynną substancję zawiera N-f[/4^metolksy-6-mety lo pirymidyny lo-2/-aminokar bony lo]-2-d wumetylokarbamoilobenzenosulfonaimid.
- 28Środek według zastrz. 26, znamienny tym, że jako czynną substancję zawiera N-[/4-metoksy-6-metylopiry midynylo -2/-aminokarbonylo ]-2-/4-morf oliny lokarbony lo/-benzeno sulfonamid.
- 29Środek według zastrz. 26, znamienny tym, że jako czynną substancję zawiera N-[/4,6-dwumetoksypirymidynylo-2-/aminokarbonylo ]-2-/1-parolidynylokarbonyloZ-benzenosulfonamid. 126 541 CL Wzór 5 Wzór 6 126 541 CH- OCH. 0 ,---( 3 . I! // A S0 2 NH-C-NH—N ’ N=( och 3 Wzór 7 CH. CH., SO 2 NH-C-NH N ; R Wzó r 8 N I R c Wzór 11 Wzór 12. (CH 2 ) 1-2 ζΤ ct cH2_ Wzór 13 A Wzór 14 O O II A CH.— Wzór 15 Wzór Ί6 126 541 CH, CH-,— (0) 0.2 CHWzór 17 Wzór 18 -CH 2 CH 2 CH 2 -S-R 12 -C-CN I CH, Wzór 23 Wzór 2^ 0' CH 2 ^CH 2 )-Q3y — N Wzór 19 Wzór 20 Wzór 25 Wzór 26 CH. (0) 0,2 R' ‘1 Wzór 2-9 -NCH. 0CHWzór 31 - ch 2 ch 2 - s-r 12 Wzór 2L Ν—N Wzór 30 Wzór 32 CH- ,R R”' Wzór 27 Wzór Ζβ o II °2 Wzó r 35 o~ CH 2 Wzór 37 Wzór 36 O~ CH 2“ Wzór 38 Wzór 33 Wzór 3h 126 541 Ν/ CH 3 •so 2 -nh-c-nh-(Q Ν· 7 coch 3 CH, Wzór 39 OCH:NSO 2 -NH- C-NH-{ę)^ 0 COCH CH: Wzór 40 OCHq SO2 NH - C — ΝΗ^ζ^)/ NCOCH: OCH 3 Wzór 43 Wzór 44 126 541 ch 3 q :-n HC^ >C=N CH3 o NH-C-NH-SO ci-ch 2 ch 2 -o-c O Wzór 48 ch 3 o x C=N Hc \\ /C-NH-C-NH-SO C—N O ch 3 o Cl-C^C^-O-Ć o Wzór 47 Wzór 49 Wzór 51 gh 3 o x C=h[ li /z~\\ < .C-NH-C-NH-SO^OJy t-N ' 7 ch 3 (CH 3 ) 2 -CH-O-C Wzór 52 126 541 CH 3°x _ o J ^-NH-Ć-NH-SOj-O) CHoO CK-iCH^-O-C CH 3 C) CH 3 -(CH 2 ) g -O-C CHoO f >-NH-i-NH-SO 2 -p CH 3 -(CH 2 ) g -O-C 0 C=N Wzór 54 Wzór 56 Wzór 55 ch 3 o z N \ θ Ν' X C-NH-C-NH-SO 2 C=N CH 3 Z CH 3 -(CH 2 )g-O-C Wzór 57 Wzór 59 126 541 c-c-ch 3 CHoO 3 \ n HC 'C-NH-C-NH-SO? 'C=N ch 3 o z Wzór 60 Cl CHoO J \ C-N HC Z *C-NH C=N ch 3 o z O li C Wzór 63 126 541 ch 3 o. CH z c- N HC' 'C b=N / ch 3 o x O C-O-CH(CH 3 ) 2 ch 3 o C-N i? N '.C-NH-C \ / C=N / nh-so 2 Wzór 65 CH 3 O x C-CMCH 2 }- 3 CH 3 C-N \V HC Z | X /C-NH-C-NH-SO 2 “(Q^ CHoO Wzór 66 ch 3 o > C=N 0 H-NH-C-NH-S0 2 /O/ C-O-fCH 2 ) 3 CH 3 XH C-N / Wzór 67 126 541 ch 3 o A ° HC 'c -nh-c-nh-so 2 C=N CH 3 O c 2 H 5 -°-c o ^-βΟ,-ΝΗ-έ-ΝΗ^ COONa Wzór 68 Wzór 70 ch 3 o. C=N v \ h 4 fl c_NH_ c _nh_s ° 2 ^Q/ CH 3 O Z c 2 H 5-°-ę O Wzór 69 O CH 3 <^so 2 -nh-S-nh^ COOH CH 3 Wzór 71 Wzór 73 Wzór 75 126 541 (CH 2 ) 2 CH(CH so 2 nhcnhΟ 3 1 Ν (' Ν Wzór 82 O-cyklo-CgH^ SO 2 NHCNH—( z N OCHCH 3 Wzór 81 Wzór 83 126 541 ° ί Η3 0-CH-CH2-(Q/ Ο so 2 nhcnh M ° CH 3 9 N ch 3 O-CH-CH^l N=< ch 3 Wzór 84 O n—z SOoNHCNH—f K CH3 OCH3 Wzór 86 O CH(CH 3 ) 2 o-ch-ch 2 ch 2 ch 3 O M 0CH3 SOoNHCNH—( N CH3 x>ch 2 O c > U N—( S0 9 NHCNH—( Ή OCH3 ch 3 Wzór 85 Wzór 87 NHCH(CH 3 ) 2 ch 3 Wzór 90 NH-CH 2 CgH5 CH 3 Wzór 91 126 541 N(CH 3 ) 2 c=o θ OCH 3 i = H,CH2) CH 3 O-SOaNHĆNH-/ 1 ^ J 0 N-/^ 3 N=< \O/ θθ2 ΝΗ0ΝΗ —( N CH-> N=< N=< CH 3 Wzór 92 ch 3 Wzór 94 O-CHCO2CH5 Wzór 95 och 3 c=0 ch 3 fol· - SO 2 N HC NH —( O N= \ SCH 2 CH2OC 2 H 5 O(CH 2 )gCH 3 Wzór 98 OCH-3 i c=o /z-x\ 9 N—/ \O?—SO 2 NHCNH— X N N==^ N(CHn) 3'2 Wzór 99 Wzór 97 126 541 och 3 Wzór 100 Wzór 102 och 3 c=o O- S0 2 NH Ć NH -<I^ N och 3 ch 2 ch 2 och 3 s C=o OCH 3 /fiL· - k \Q/ so 2 nhcnh—( J ch 3 Wzór 101 Wzór 103 Wzór 104 OCH-CHoCl Wzór 105
Independent claims29
1,412 paragraphs in 4 sections, as filed
PATENT DESCRIPTION
<img file="PL126541B1_D0001.tif" />
URZĄO
PATEHTOWT
PRL
Additional patent to patent No.-1 - Patent pending: 29.05.79 (P. 215949)
Priority: 30.05.78 for claims 2-7
30.11.78 for claims 8-13; 27
01.03.79 for 17, 19, 20, 23-25, 28, 29
13.04.79 for claims 1, 14-16 18, 21, 22, 26
United States of America Patent application was announced: 25.02.80 Patent description published: 1985 08 31 Int. Cl<sup>3</sup> A01N 41/06
<img file="PL126541B1_D0002.tif" />
Inventor: Patent holder: EI Du Pont De Nemours and Company, Wilmington (United States of America)
Agent for controlling undesirable vegetation and
The present invention relates to an agent for controlling undesirable vegetation containing as active substance a new N-7 heterocycloamino carbonyl / aryl sulfonamide derivative.
From Dutch Patent No. 121788 is known a process for the preparation of compounds of general formula II, in which R1 and R<sub>2</sub> they are the same or different and are alkyl radicals with 1 to 4 carbon atoms, and R3 and R4 are the same or different and are hydrogen, chlorine or alkyl radicals with 1 to 4 carbon atoms. These compounds are used as active herbicidal substances with general or selective action.
From the patent specification Ser. Am. No. 3637366 compounds of the general formula (III) are known in which R 1 is a hydrogen atom or a lower saturated aliphatic acyl radical and R<sub>2</sub> represents a hydrogen atom, a 2-pyrimidinyl, pyridyl, amidine, acetyl or carbamoyl group. These compounds regulate the development of such plants as blooder, finger pepper, chicory, clover and annual panicle.
French Patent No. 1,468,747 discloses para-substituted phenylsulfonamides of formula 4 in which R is hydrogen, halogen, -CF3, or an alkyl radical. These compounds counteract diabetes.
In the Logemann et al. Publication, Chem. Ab. 53, 18052 g (1959) discloses numerous sulfonamides, including uracil derivatives and compounds of formula 5 in which R is a butyl or phenyl radical or a group of formula 6 in which Rj is a hydrogen atom or a methyl radical . Studies conducted with these compounds in rats (oral dose of 25 mg (100 g) showed that the highest ability to reduce blood sugar is those compounds of formula 5 in which R is a radical (butyl or phenyl, while others work poorly or not) operate at all J. Wojciechowski, Acta Polon. Pharm. 19, p.
121-125 (1962) and [Cheim. Ab., 59, 1633e) describes the synthesis of Ni [/ 2,6-dimethoxypi<sub>and</sub>rimidinyl-4 - / - aminocarbonyl] -4-methylbenzenesulfonamide of formula 7 and based on the similarity to the known compound, this author speculates that the compound of formula 7 may have the ability to reduce blood sugar.
Substituted pyrimidinylsulfonylureas of formula 8 in which R is a hydrogen atom or a methyl radical, which also has a para substituent on the phenyl ring, are described in Farmco Ed. Sci., 12,586 (1957) [Chem. Ab., 53, 18052 g (1959)].
The occurrence of undesirable vegetation causes significant damage to cultivated plants, especially in crops intended to satisfy basic human needs in the field of food and being a source of fiber, e.g. <sup>30</sup> like cotton, rice, corn, wheat etc. Growth
126 541
126 541 population and the accompanying global shortage of food and fiber require an increase in the productivity of these crops.
Preventing loss or reducing losses in such crops by inhibiting the growth of unwanted vegetation or destroying this vegetation is one way to increase the yield of these crops. Numerous means are known for destroying weeds or inhibiting (regulating) their growth. These agents are known as herbicides. However, there is still a need to invent more effective herbicides.
The agent according to the invention is a herbicidal agent which is able to control weeds generally or selectively before or after emergence of plants and as a regulating agent for plants.
^ ecW ^ of this agent is that, as the active substance, it contains a new compound of the general formula I, in which Q is an oxygen or sulfur atom or a group of formula 9, wherein when Q is an oxygen or sulfur atom, then R is an alkyl radical of 1-12 carbon atoms, an alkyl radical with 2-6 carbon atoms, containing 1-4 substituents, of which at most 3 are fluorine, chlorine or bromine, at most 2 is methoxy and at most 1 is cyano, or R is an alkenyl radical of 3-10 carbon atoms, an alkenyl radical of 3-6 carbon atoms substituted by 1-3 fluorine, chlorine or bromine atoms, or R is a group -CH<sub>2</sub>CN, —CH<sub>2</sub>WHAT<sub>2</sub>CH3, —CH<sub>2</sub>WHAT<sub>2</sub>C<sub>2</sub>H<sub>5</sub>, cycloalkyl radical with 5-8 carbon atoms, cycloalkenyl radical with 5-8 carbon atoms, cycloalkyl radical with 5-6 carbon atoms substituted with 1-4 methyl, methoxy, alkyl groups with 2-4 carbon atoms or fluorine, chlorine or bromine atoms or R is a cycloalkylalkyl radical of
4-10 carbon atoms, cycloalkylalkyl radical with
4-8 carbon atoms substituted by one or two methyl groups, a dicycloalkenyl radical of 7-10 carbon atoms, a tricycloalkyl radical of 10 carbon atoms, a tricycloalkenyl radical of 10 carbon atoms, a dicycloalkyl radical of 7-10 carbon atoms, a group of formula 10 in which Rg is an alkyl radical of 1-3 carbon atoms or a hydrogen atom and Rio and Rn are the same or different and represent hydrogen atoms, alkyl radicals of 1-3 carbon atoms, chlorine or bromine atoms, the —OCH group<sub>3</sub> or —OC<sub>2</sub>H<sub>5</sub>or R<sub>10 </sub>and Rn together represent a five- or six-membered ring of formula 11 or 12, and n in formula 10 represents the number zero, 1, 2 or 3, where the total number of carbon atoms is at most 12, or also R represents a group of formula 13, 14, 15, 16, 17, 18, 19, 20 or 21, wherein in formula 14 A is oxygen or sulfur and Aj in formulas 13, 17, 18, 20 and 21 is oxygen or sulfur or SO2, and when Q is an oxygen atom, then R can also be a hydrogen atom, an alkali metal atom generally designated with the letter M or a group of formula -CH<sub>2</sub>CH<sub>2</sub>OR<sub>7</sub>, —CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OR7, CH / CH3 / CH2OR7, in which R<sub>7</sub> means the group -CH<sub>2</sub>CH<sub>3</sub>, —CH / CH3 / 2, phenyl group, —CH group<sub>2</sub>CH<sub>2</sub>C1 or —CH<sub>2</sub>CO1<sub>3</sub>or R is a group of formula / CH<sub>2</sub>CH<sub>2</sub>ABOUT/<sub>n</sub>, Rg or [—CH / CH3 / CH<sub>2</sub>ABOUT-]<sub>n</sub>, Rg, in which formulas Rg is the group —CH3, —CH2CH3, —CH / CHg /<sub>2</sub>, phenyl group, —CH group<sub>2</sub>CH<sub>2</sub>C1 or CH2CCI3, and ń is the number 2 or 3, where the total number of carbon atoms in the R substituent is at most 13, or R is a group of formula 22 or 23, in which formulas Ri<sub>2</sub> means the group -CH<sub>3</sub>, —CH<sub>2</sub>CH<sub>3</sub>, —CH / CH3 / 2 or a phenyl group, and when Q is a group of formula 9, then R is a hydrogen atom, an alkyl radical of 1-12 carbon atoms or a group of formula / —CHaCHaO / n ,, R12 or ~ -CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OR<sub>12</sub>in which it is Ri<sub>2</sub> in the first of these formulas is the number 1-3, or R is an alkenyl radical of 3-10 carbon atoms, a cycloalkyl radical of 3-8 carbon atoms, a cycloalkyl radical of 5-8 carbon atoms having 1-8 3 substituents, of which at most 2 are methoxy groups, and the others are methyl or ethyl groups, or R is a cycloalkenyl radical with 5-6 carbon atoms, a trifluoromethylcyclohexyl radical, a cycloalkylalkyl radical with 4-10 carbon atoms, * cycloalkylalkyl radical with 4-8 carbon atoms, substituted by 1 or 2 methyl radicals, or R 0 is a group - CH<sub>2</sub>CN, group —CH<sub>2</sub>CH<sub>2</sub>CN, group of formula 24, group -OCH3, group -N1 / CH3Ą, group of formula 10 in which n, R9, Rio and Rn are as defined above, group of formula 25 or 26, group of formula 27 in which R 'is a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms, a methoxy radical, a fluorine, bromine or chlorine atom, a —CF3, —CN, —NO group<sub>2</sub>, —RSO<sub>2</sub>CH3, - SCHg or —N / CH3 / 2, R is a hydrogen atom, a 1-4 alkyl radical, a methoxy group or a fluorine, bromine or chlorine atom and R 'is a hydrogen atom, a methyl radical or a chlorine, fluorine atom or bromine, Rg in formula 9 is a hydrogen atom, an alkyl radical of 1-6 carbon atoms, an alkyl radical, a group -CH<sub>2</sub>CN or —CH<sub>2</sub>CH<sub>2</sub>CN or Re and R together represent the group / CH2 / 4, / CH2 / 5, / CH<sub>2</sub>/<sub>6</sub>, —CH2CH2OCH2CH2— or —CH<sub>2</sub>CH<sub>2</sub>N / CH3 / / CH<sub>2</sub>CH<sub>2</sub>- wherein when R is methoxy, then Re is methyl and when Rg is -CH<sub>2</sub>CN or —CH<sub>2</sub>CH<sub>2</sub>CN, then R is the group -CH<sub>2</sub>CN albe —CH<sub>2</sub>CH<sub>2</sub>CN, and R together with R<sub>6</sub> have a maximum of 13 carbon atoms, Ri in formula 1 is a group of formula 28, 29 or 30, wherein in formulas 29 and 30 Xj is a hydrogen or chlorine atom, the group -OCH3, - ^ OCH<sub>2</sub>CH<sub>3</sub> or —CH3 and Yi represent a hydrogen atom, —OCH3 or —CH3 group, but Xj and Yi are not simultaneously hydrogen and when Ri is a group of formula 29 or 30 then R4 and R5 in formula 1 are hydrogen and R contains less than 6 carbon atoms; in formula 28, X is hydrogen or chloro, -CH3, -OCH<sub>3</sub>, —OCH<sub>2</sub>CH<sub>3 </sub>or -OCH2CH2OCH3 and Y is a hydrogen or chlorine atom, an alkyl radical with 1-4 carbon atoms, an alkyl radical with 1-4 carbon atoms substituted with the group -OCH3, -OC<sub>2</sub>H<sub>5</sub>, —CN, —CO<sub>2</sub>CH<sub>3</sub>, -WHAT<sub>2</sub>C<sub>2</sub>H5 or Ί — 3 fluorine, chlorine and bromine atoms, or Y is an alkenyl radical of 3—
126 541 carbon atoms, the --CH radical<sub>2</sub>C = CRia in which
Ris is hydrogen, -CH3 or -CH<sub>2</sub>C1 or Y is a group of formula -A- / / CHy<sub>n</sub>, —Aj— (alkyl with 1 ^ 3 carbon atoms) in which n ', A and Αχ are as defined above, or Y is a group of formula -ACH<sub>2</sub>C / O / —L, —AC / CHj / HC / O / —L or —ACH<sub>2</sub>CH<sub>2</sub>C / O / —L, in which formulas L is —NH<sub>2</sub> or a group of formula III, a group of formula -NH / alkyl
1-4 carbon atoms, —N / alkyl with 1-4 carbon atoms / 2 or an alkoxy group with 1-6 carbon atoms, and A has the above meaning, or Y is a group —SCN, N3, a group of formula NRieRij, wherein Rig is a hydrogen atom or a methyl radical and R17 is a hydrogen atom or a "methoxy" radical, an alkyl radical of 1) -4 carbon atoms, an alkyl radical of 1-4 carbon atoms substituted with a —CN group, a —CO2CH3 or CO2C2H5 group, or R17 is an alkyl radical with 2-3 carbon atoms substituted with -OCH3 or -OC<sub>2</sub>H $, «or R17 represents an alkenyl radical with 3-4 carbon atoms, or Ry and R17 together represent the group —CH3CH2CH2CH2— or —'CH2CH2OCH2CH2— or also Y represents a group of the formula —O — Rk wherein Ry represents an alkyl radical with 1-4 carbon atoms, an alkyl radical with 2-4 carbon atoms substituted with 1-3 fluorine, chlorine or bromine atoms, an alkyl radical with 1-4 carbon atoms substituted with a cyano group, an alkenyl radical with 3-4 carbon atoms or a radical of formula CH<sub>2</sub>C = CRi3 in which R13 is as defined above, or Y is a group of formula 32, a group of formula -SRjg in which R15 is an alkyl radical of 1-4 carbon atoms, an alkyl radical of 1-2 carbon atoms substituted with a cyano group , an alkyl radical or a propairgyl radical, wherein when Y has 4 or more carbon atoms, then R contains less than 5 carbon atoms, and when X is chlorine, and Y is chlorine, and when X and Y are hydrogen . then R contains less than 5 carbon atoms, Z is = CH or nitrogen, in addition, in formula 1 R<sub>2</sub> is hydrogen, chlorine, bromine or fluorine, an alkyl radical with 1-3 carbon atoms, the group -4iO<sub>2</sub>, —SO2CH3, —OCH<sub>3</sub>, —SCH3, —CF ,, —N / / CH3 / 2, —NH<sub>2</sub> or —CN, R3 is a hydrogen, chlorine, bromine or fluorine atom or a methyl radical, R <is a hydrogen atom or a methyl radical, Re is a hydrogen atom, a methyl or methoxy radical and W is an oxygen or sulfur atom,
In the compositions according to the invention, the compounds of the formula I are in the form of free compounds or in the form of their agricultural acceptable salts, e.g. sodium, potassium or alkylammonium salts or salts with trichloroacetic acid.
The following groups of compounds of formula I have particularly advantageous properties.
2. Compounds of formula 1 in which R <and Rg are hydrogen, W is oxygen and the carbon atom in the R substituent attached to the Q substituent is also bonded to at least one hydrogen atom.
3. Of the compounds of group 2, especially those in which R is preferred<sub>2</sub> represents a hydrogen, chlorine, bromine or fluorine atom, an alkyl radical of 1-3 carbon atoms, the group -NO<sub>2</sub>, —OCH<sub>S</sub>, —SCH ,, - ^ SO<sub>2</sub>CH<sub>3</sub>, —CF<sub>3</sub>, -4J / CH3 / 2, —NH<sub>2</sub>, —CN and R<sub>S </sub>is hydrogen and is in a para position relative to the sulfone group,
4. Of the compounds of group 3, particularly preferred properties are those in which Q is an oxygen or sulfur atom and R is an alkyl radical with 1-6 carbon atoms, an alkenyl radical with 3-6 carbon atoms, an alkyl radical with 2-4 carbon atoms having 1 —4 substituents, of which at most 3 are fluorine and chlorine, at most 2 are —OCH3 and at most 1 is —CN, or R is —CH<sub>2</sub>CN, an alkenyl radical with 3-4 carbon atoms substituted with 1-3 chlorine atoms, a cycloalkyl radical of 5h-6 carbon atoms, a cycloalkenyl radical with 5-6 carbon atoms, a cycloalkyl radical with 5-6 carbon atoms containing 1-4 substituents such as methyl, methoxy, ethyl or chlorine radicals, or R is a cycloalkylalkyl radical with 4-7 carbon atoms, a group of formula 10 in which Rg is a hydrogen atom or a methyl radical, n is zero or 1, and Rio and Rn are the same or different and are hydrogen or chlorine, methyl or methoxy radicals, or R is a group of formula 33, 34, 35, 36, 37 or 38.
5. Of the compounds of group 3, those in which Q is an oxygen atom and R is a hydrogen atom or an alkali metal atom or a group of the formula -CH are especially valuable<sub>2</sub>CH2OR7, —CZCH3 / HCH<sub>2</sub>OR7 or —CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OR7, in which formulas R7 has the above meaning, or R is a group of formula / CHsGHsOi / sRg or [C / CH3 / HCH<sub>2</sub>ABOUT]<sub>2</sub>Rg, in which formulas Rg is an alkyl radical with 1-3 carbon atoms or the -CH radical<sub>2</sub>CH<sub>2</sub>C1.
6. Of the compounds of group 3, those in which Q is a group of formula 9, wherein Rg is a hydrogen atom, an alkyl radical with 1-3 carbon atoms, the group -CH<sub>2</sub>CN, —CH<sub>2</sub>CH<sub>2</sub>CN or —CH<sub>2</sub>CH = CH<sub>2</sub> or Rg together with R form a group of formula -CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>-, —CH<sub>2</sub>CH<sub>2</sub>EH<sub>2 </sub>CH<sub>2</sub>CH<sub>2</sub>—- or —CH<sub>2</sub>CH<sub>2</sub>2 CH<sub>2</sub>- and R represents a hydrogen atom, an alkyl radical with 1-6 carbon atoms, a group of formula -CH<sub>2</sub>CH<sub>2</sub>ORn or -CHsCI ^ CHsORn, in which Rgg has the meaning given above, or R is an alkenyl radical with 3-6 carbon atoms, a cycloalkyl radical with 3-6 carbon atoms, a cycloalkenyl radical with 5-6 carbon atoms, a cycloalkyl radical with 6 carbon atoms substituted with 1-2 methoxy groups or 1-3 methyl or ethyl groups, or R is a trifluoramethylcyclohexyl group, a cycloalkylalkyl group with 4-7 carbon atoms, and - CH group<sub>2</sub>CN, = —CH<sub>2</sub>CH<sub>2</sub>CN or -OCH, a group of formula 24, a group of formula 27 in which R 'is a hydrogen atom, R is a hydrogen atom, an alkyl radical of 1-4 carbon atoms, a methoxy group or a fluorine, bromine or chlorine atom, and R 'is a hydrogen, chlorine, fluorine or bromine atom or a methyl radical, or R is a group of formula 10 in which n is zero, Rg is a hydrogen atom or a methyl radical 126 541
Iowa, and Rio i. Rn are the same or different and are hydrogen, methyl, chlorine or metesyl.
7. Of the compounds of group 3, favorable properties have those in which X is -CH<sub>S</sub>, —OCH<sub>3 </sub>or -OC<sub>2</sub>H<sub>5</sub> and Y is a hydrogen atom, an alkyl radical with 1-4 carbon atoms, an alkyl radical with 1-2 carbon atoms substituted with the group -OCHg, -OC<sub>2</sub>H<sub>5</sub>, —CN, - ^ CO<sub>2</sub>CH<sub>3</sub> or —CO<sub>2</sub>C<sub>2</sub>H<sub>5</sub> or 1-3 fluorine or chlorine atoms, or Y is an alkenyl radical of 3-4 carbon atoms, the group -OCH<sub>2</sub>WHAT<sub>2</sub> (alkyl radical with 1-4 carbon atoms), group --OC7CHaZHCO<sub>2</sub> (an alkyl radical with 1 to 4 carbon atoms) or an —OCH group<sub>2</sub>CH<sub>2</sub>WHAT<sub>2 </sub>(an alkyl radical with 1 to 4 carbon atoms), or Y is a group -OCH<sub>2</sub>CH<sub>2</sub>O (an alkyl radical with 1-3 carbon atoms) or the group -OCH<sub>2</sub>CH<sub>2</sub>CH<sub>2 </sub>(alkyl radical with 1 ^ 3 carbon atoms), or Y is a group of formula -OR ^, in which Ru is an alkyl radical with 1-4 carbon atoms, an alkyl radical with 2-3 carbon atoms substituted
1-3 fluoro or chloro atoms or an alkyl radical of 1-3 carbon atoms, substituted with a group, or Ru is an alkenyl radical of 3-4 carbon atoms or Y is a group -SCH<sub>2</sub>, group —SC<sub>2</sub>H<sub>3</sub> or a group of formula -NRuRn in which Ru is a hydrogen atom or a methyl radical, R17 is an alkyl radical with 1-4 carbon atoms, an alkyl radical with 1-4 carbon atoms substituted with the group -CN, an alkyl radical with
2 to 3 carbon atoms substituted with the group -OCH<sub>3 </sub>or -OC<sub>2</sub>Hs, or an alkenyl radical with 3-4 carbon atoms, and Xj and Yi have the meanings given above.
β. Of the compounds of group 7, those in which —QR has the meaning given for compounds of group 4 are preferred.
9. Of the compounds of group 7 are also preferred those in which —QR has the meaning given for the compounds of group 5.
10. Of the compounds of group 7, favorable properties also have those in which - QR has the meaning given for the compounds of group 6.
11. Of the compounds of groups 8, 9 and 10, those in which R is particularly preferred<sub>2</sub> represents a hydrogen or chlorine atom or a methyl radical.
l2. Of the compounds of group 11, especially preferred are those in which Q is an oxygen or sulfur atom and R is an alkyl radical with 1-4 carbon atoms, an alkenyl radical with 3-4 carbon atoms, an alkyl radical with 2-3 carbon atoms substituted with —OCH3, chlorine or —CN, or R is —CH<sub>2</sub>CN, an alkenyl radical with 3 carbon atoms substituted with 1 to 3 chlorine atoms, a cycloalkyl radical with 5 to 6 carbon atoms, a cyclohexenyl radical, a cyclohexyl radical substituted with 1 to 3 methyl radicals, or a group of formula 10ζ in which is a hydrogen atom or a methyl radical in is zero or 1, and Rio and R11 are the same or different and are methyl or methoxy radicals or chlorine atoms.
13. Particularly preferred are those compounds of group 11 in which Q is oxygen and R is hydrogen or alkali metal or a group of formula -CH<sub>2</sub>CH<sub>2</sub>OR7, in which R7 is the radical -CH<sub>2</sub>H5, —CH / CH<sub>3</sub>/<sub>2</sub>, phenyl radical, -CH radical<sub>2</sub>CH<sub>2</sub>C1 or ~ -0Η / ΟΗ<sub>3</sub>/ 0Η<sub>2</sub>Ο0<sub>2</sub>Η5.
14. From group 11, also preferred are compounds in which Q is a group of formula 9 in which Re is a hydrogen atom, a methyl or ethyl radical and R is an alkyl radical with 1-4 carbon atoms, the - CHaCH radical<sub>2</sub>OCH<sub>3</sub>, —CH<sub>2</sub>3 OC<sub>2 </sub>H5, an alkenyl radical with 3 to 4 carbon atoms, a cycloalkyl radical with 5 to 6 carbon atoms, a cyclohexyl radical substituted with 1 to 3 methyl radicals, a group of visor 27 in which R 'is a hydrogen atom, R is a hydrogen or chlorine atom or a radical methyl and R 'is hydrogen or chloro or a methyl radical, or R is a group of formula 10 in which n is zero, and R $, R10 and Rn are hydrogen, or R and Re together form the radical -CH<sub>2</sub>CH<sub>2</sub>CN<sub>2</sub>CH<sub>2</sub>- or —CHjCHzOCHACHz—.
15. Preferred properties are those of the compounds of group 11 in which R1 is a group of formula 28, in which X is —CH3, —OCH<sub>3</sub> or -OC3H5, Z is a group = GH or a nitrogen atom, and Y is a hydrogen atom, an alkyl radical of 1-3 carbon atoms, the group -CH<sub>2</sub>OCH<sub>3</sub>, —CH<sub>2</sub>OC<sub>2</sub>H<sub>5</sub>, —OCH<sub>2</sub>WHAT<sub>2 </sub>(alkyl radical with 1-2 carbon atoms) —OC / CH® / HCO<sub>2</sub> (alkyl radical with 1-2 carbon atoms) or -O / alkyl radical with 1-3 carbon atoms / or -O / alkenyl radical with 3-4 carbon atoms, or Y is a group of formula -NRujRn, in which Rie is a hydrogen atom or a methyl radical, and R17 is an alkyl radical of 1-3 carbon atoms.
16. Compounds of group 15 are preferred, wherein —QR is as defined for compounds of group
12.
17. Compounds of group 15 are also preferred, wherein —QR is important for group 13 compounds.
18. Compounds of group 15 are also preferred, wherein —QR is as defined for compounds of group 14.
19. Compounds of groups 16, 17 or 18 in which R is preferred<sub>2</sub> and R3 are hydrogen.
twenty. From group 19, compounds in which Q is an oxygen atom and R is an alkyl radical with 1-4 carbon atoms, an alkenyl radical with a
3-4 carbon atoms, an alkyl radical of 2-3 carbon atoms with chlorine, a group of formula --CH<sub>2</sub>CH<sub>2</sub>O / CH<sub>3</sub>C<sub>2</sub>H5 /, —C / CH3 / HCH2O / CH3, C<sub>2</sub>H<sub>5</sub>/ or with the formula —0113011301130 / 0113.03115 /.
21. From group 19, compounds in which Q is a sulfur atom and R is an alkyl radical with 1-4 carbon atoms or an alkenyl radical with 3-4 carbon atoms are preferred.
22. Compounds of the group have advantageous properties
19, in which Q is a group of formula 9, in which Re is a hydrogen atom or a methyl radical and R is an alkyl radical, 1-4 carbon atoms, an alkenyl radical with 3-4 carbon atoms, the group —CH2CH2O— / CH ^ CzHe / or —CH<sub>2</sub>CH<sub>2</sub>CH<sub>2 </sub>O / CH 3, C<sub>2</sub>H5 /, or R and Re together represent a group or a group -CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>—.
23. From group 19, those compounds wherein X is a methyl, methoxy or radical are preferred
126 541 ethoxy and Y is an alkyl radical of 1-3 carbon atoms, methoxy radical, ethoxy radical, —OCH group<sub>2</sub>WHAT<sub>2</sub>- / CH3, C<sub>2</sub>Hg /, —OC / CH3 / / HCH<sub>2</sub>^ CO / CH<sub>3</sub>C<sub>2</sub>H5 / or CH<sub>2</sub>OCH<sub>3</sub>.
24. From group 23, compounds in which —QR has the meaning given for compounds from group 20 are preferred.
25. From group 23, compounds in which —QR has the meaning given in group 21 are preferred.
26. From group 23, favorable properties also have compounds in which —QR has the meaning given as being preferred in group 22.
The following compounds have particularly advantageous properties:
N- [4,6-dimethylpyrimidinyl-2 - / - aminocarbonyl]] -2-ammonium carbonobenzene sulfonamide,
N- [4,6-dimethyl-1,3,5-triazinyl-2-aminocarbonyl] -2-am carbonobenzene sulfonamide,
N - [/ 4-metokBy-6-smetylopiryimidynylo-2 / aminocarbonyl] -2-metoksykarbonylobenzenosulforiamid.
N - [/ 4-methoxy-6-methyl-l, 3,5-triazin-27-aminocarbonyl] -2-metoksykarbonylbbenzenosulfonamid.
N- [74,6-dwumetoksypirymidynylo-2 / aminocarbonyl] -2-metoksykarbonylobenzenosulfonamid.
N - [/ 4,6-dimethoxy-l, 3,5-triazynyio ^ 2 / aminocarbonyl] -2-metoksykarbonylobenzenosulfonamid.
N - [/ 4,6-d vuimethoxy-3,5-triazinyl-2-aminiminocarbonyl] -2- (isopropoxycarbonyl) benzenesulfonamide, N - '[/ 4-methoxy-6-methyl-1,3 5-triazin-2 / s<sup>,</sup>nocarbonyl] -2- (opoxycarbonyl) benzenesulfonamide isopropyl,
N - [/ 4,6-dimethoxy-1,3,5-triazine-2,2-aminocarbonyl] -2-72-chloroethoxycarboxyl-7-benzenesulfonamide,
N - [74-toxy-6-methyl-1,3,5-triazine-2-aminocarbonyl] -2- (2-chloroethoxycarbonyl) -benzenesulfonamide,
N - {/ 4-methoxy-6-methyl-1,3,5-triazinyl-2-amino-carbonyl] -2-propoxycarbonylbenzenesulfonamide, N - [/ 4-methoxy-6-methylpyrimidinyl-2 / - aiminocarbons lo] -2- / 2-C chloro toxic carbonates lo / benzene sulfide for namid,
N - [/ 4-methoxy-6-methyl-1,3-triazinyl-2-aminocarbonyl] -2- (2-phenyl-1-methylethoxy carbonyl) benzenesulfonamide,
N - [/ 4-methoxy-6-methyl-l, 3,5-triazin-2 / -aiminokarbonylo] -2- [2-72-chloroethoxy / -etbksykarbonylo] -benzenesulfonamide,
N - [/ 4-methoxy-6-methyl-l, 3,5-triazin-2 / amino<sup>and</sup>carbonyl] -2- / 2-etoksyetoksykarbonylo / -benzenesulfonamide,
N - [/ 4-methoxy-6-methyl-1,3,5-triazinyl-2 / -aminocarbonyl] -2-allyloxycarbonylbenzenesulfonamide, N- [74-methoxy-6-methylpyrimidinyl-2 / aminocarbonyl] -2 -diminoylcarbamoylbenzenesulfonamide, N - {{4-methyl-6- / 1-m toxins, carbonyls are x / -parimidinyl-2] -aminocarbonyl) -2-methoxycarbonylbenzenesulfonamide,
N {[4-methyl-6- (1-methoxycarbonylethoxy) -1,3,5, -triazinyl-2] aminocarbonyl} -2-methoxycarbonylbenzenesulfonamide,
N - [/ 4-methoxy-6-methyl-1,3,5-triazinyl-2-aminqcarbonyl] -2-methylthiocarbonylbenzenesulfonamide, N - [/ 4-methoxy-6-methyl-1,3,5-triazinyl -2-amino-10-carbonyl] -2-L-isopropylthiocarbonylbenzenesulfonamide,
N - [/ 4-methoxy-6-methylpyrimidinyl-2 / -aminocarbonyl] -2-isopropylthiocarbonylbenzenesulfonimide, N- [74-methoxy-6-methyl-1,3,5-triazinyl-27-aminocarbonyl] -2- / 2 -mylpropoxycarbonyl / benzenesulfonamide,
N- [74-toxy-6-methylpyrimidinyl-27-aminocarbonyl] -2-74-nK> rfolinylaminocarbonyl / benzenesulfonamide,
N- [/ 4,6-d vumethoxypyrimidinyl-2 / -amino carbonyl] -2-71-pyrrolidine locarbonylZ-benzenesulfonamide and N- [/ 4,6-d vumethoxypyrimidinyl-2 / -aminocarbonyl] -2- / allyloxycar bony l-benzenesulfonamide.
The compositions according to the invention containing the compounds of formula I are prepared by known methods. These agents are in the form of dusts, granules, lumps, suspensions, emulsions, wettable powders, emulsifiable concentrates, etc. Many of them can be used directly. Spraying agents can be diluted with appropriate substances and sprayed in an amount of a few to several hundred liters per 1 ha.
The compositions according to the invention contain in a weight ratio of about Ojl-99% active substance or substances of formula I and at least one surface-active substance in an amount of about 0.1-20% and a solid or liquid diluent in an amount of about 1-99.9% . The preferred overall composition of the compositions according to the invention is given in Table 1 in weight percent, taking the active substance and at least one surfactant or diluent for 100%.
Table 1
<td rowspan="2">Type agent</td><td colspan="3">The content of ingredients in% by weight</td>
<td>substance The active</td><td>dilution diluents</td><td>surface-active substance on</td>
<td>Wetable powders</td><td> 20—90</td><td> 0—74</td><td>H-10</td>
<td>Oil suspensions, emulsions and emulsifiable concentrates</td><td> 3—50</td><td> 40—95</td><td>0-Ί5</td>
<td>suspensions Water</td><td> 10—50</td><td> 40—84</td><td>li-20</td>
<td>(Dusts</td><td> 1—25</td><td> 70—99</td><td> 0— 5</td>
<td>Granules and clumps</td><td> 0,1—95</td><td> 5—99,9</td><td> 0—15</td>
Depending on the manner in which the product is to be used and depending on the nature of the active substance, products containing more than or less than
126 541 amounts in Table 1, within the above limits. Sometimes it is also preferable to use surfactants in an amount greater than that given in the table, these substances being introduced into the preparation during its manufacture or mixed with the preparation in the tank before applying the agent.
Some typical solid diluents are described in Watkins et al., Handbook of Insecticide Durt Diluents and Cerriers, 2nd Edition, Dorland Books, Caldwell, New Jersey, but other solid diluents can also be used. For the production of wettable powders, it is preferable to use thinners with a higher absorption capacity, while for the production of dusts, higher-density thinners are more suitable.
Typical liquid diluents are known from Marsden's publication, Solvents Guide, 2nd Edition, Intersoience, New York, 1950. Suspension concentrates and preferably have a solubility of less than 0.1%, and concentrates for solution preparation should provide solutions that do not separate into phases at 0 ° C.
In the work "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp. Ridgewood, New Jersey, and in Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc. New York, 1964, a list of surface active substances and recommended range of use is given. The compositions according to the invention may contain small amounts of anti-foam additives, caking, corrosion and the development of microorganisms.
The compositions according to the invention are prepared by known methods. Solutions are prepared by simply mixing the ingredients. Solid products with high fineness are made by mixing the ingredients and usually grinding them in a hammer or fluid mill.
iSuspensions are prepared by wet milling, e.g. as described in U.S. Pat. No. 3060084. Granules and lumps can be made by spraying the active substance onto previously prepared granular carriers or by agglomeration, e.g. given in the article by JE Browning, "Agglomeration", Chemical Engineering, December 4, 1967, p. 147 et seq., or in "Perry's" Chemical Engineer's Handbook, 4th Edition, McGraw-Hill, New York, 1963, pp. 8-59 et seq.
Further information regarding the preparation of the agents is given e.g. in U.S. Patent No. No. 3235361, column 6, line 16 to column 7, line 19 and examples 10-41, US Patent No. No. 3309192, column 5, line 43 to column 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182, in U.S. Patent No. Am. No. 2891855, column 3, line 66 to column 3, line 17 and examples 1-4, in section GX2. Klingman, "Wood Control ans a Science," John Wiley and Sons, Inc. New York, pp. 81-98 and in the section of JD Fryer and SA Evans, "Weod Kontrol Hand12 book", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Examples I-X give examples of agents of the invention, unless otherwise indicated, the parts and percentages given in these examples are parts or percent by weight. , {Example I. A wetable powder.
N - [/ 4,6-dimethoxypyrimidinyl-2 / -aminocarbonyl] -2-methoxy-benzenesulfonamide 95.
Dioctyl sodium sulfosuccinate 0.1 · / ·
Sodium Lignin Sulphonate 1%
Synthetic silica silica 4 · / ·
The above ingredients are mixed and ground in a hammer mill until all particles smaller than 100 microns in diameter are obtained, after which the product is sieved and packaged.
Example II Granular agent.
The wetable powder of example I 10 · / · Granular attapulgite 0.84-0.42 mm 90 · / ·
A suspension of wettable powder containing 50 * / · solids is sprayed onto the surface of the granular attapulgite in a double cone mixer.
Example III. Wetable powder. N - [/ 4-methyl-6-methoxy-1,3,5-triazinyl-2-aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 40%
1.5% sodium dioctyl sulfosuccinate
Low viscosity methyl cellulose 1.5 · / ·
Atapulgit 54 · / ·
Sodium Lignin Sulphonate 3%
The ingredients are mixed thoroughly and passed through an air mill until particles smaller than 15 microns are obtained, then again mixed and sieved through a No. 50 screen (0.3 mm holes) and then packed.
Example IV Granular agent.
The wetable powder of example I 25 Vo
Gips 64 · / ·
Potassium sulfate 11%
The ingredients are mixed in a rotary mixer by spraying the water necessary for the granulation process onto them and when most of the grains reach 1.0-0.42 mm (sieves No. 18-40 on the US scale) the product is dried and sieved. Too large grains are crushed again until the desired size is obtained. The granular composition obtained contains 10 * / · active substance.
Example V. A wetable powder. N - [/ 4,6-dimethoxy-1,3,5-triazinyl-2 - aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 65%
Polyethylene glycol with dodecylphenol 2 · / ·
Sodium lignin sulfonate 4 · / ·
Sodium silicon glycidate 6 · / ·
Roasted Montanorillonite 23 · / ·
The solid components are mixed thoroughly by spraying the liquid components in a mixer, then ground in a tai hammer mill to obtain a product whose majority of the particles is less than 100 microns, after which the product is mixed again, passed through a sieve with 0 holes 3
126 541 mm (sieve No. 50 according to the US scale) and packs.
Example VI. Suspension in oil.
N - [/ 4-methyl-6-methoxypyrimidinyl-2 / -aminocarbonyl] -2-methoxy, carbonylbenzenesulfonamide 25%
Addition product of polyoxyethylene with 5% sorbitan hexahydrate
70% higher aliphatic hydrocarbon oil
Ingredients are angel until particles smaller than about 5 microns are obtained. The resulting suspension can be used directly, but it is preferably further diluted with oils or emulsified with water.
Example VII. Suspended suspension. N - [/ 4,6-dimethyl-1,3,5-triazinyl-2-aminocarbonyl] -2-methoxycarbone lobenzenesultonamide 25%
Hydrated attapulgite 3%
Raw calcium lignin sulfonate 10%
Sodium dihydrogen phosphate 0.5%
Water 61.5%
The ingredients are ground in a ball or roller mill until solid particles less than 10 microns in diameter are obtained, and then the product is packaged.
Example VIII. Tablet extrusion. N - [/ 4,6-dimethylpyrimidinyl-2 / -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 25%
Anhydrous sodium sulfate 10%
Crude 5% calcium lignin sulfonate
Sodium alkylnaphthalenesulfonate 1%
Calcium-magnesium bentonite 59%
The ingredients are mixed and ground in a hammer mill, sprinkled with about 12% water and extruded in the form of a cylinder with a diameter of about 3 mm, after which it is cut into sections of about 3 mm in length.
These tablets can be used immediately after drying, or after drying, they are comminuted to pass through a sieve with 0.84 mm openings (No. 20 sieve on a scale used in the United States AmJ. Grains retained on a sieve in 0.42 mm openings (sieve No. 40) can be packed as a finished product, and fine particles can be recycled.
• Example IX. Solution. N - [/ 4,6-dimethoxy-1,3,5-triazinyl-2 / -aminocarbonyl] -2-methoxybenzenesulfonamide 5%
Dimethylformamide 95%
The ingredients are mixed to form a solution that can be used with very low volume techniques.
Example X. A wetable powder.
N - [/ 4,6-dimethylpyrimidinyl-2 / -aminocarbonyl] -2-methoxycar, bonylbenzenesulfonamide 80%
Sodium alkylnaphthalenesulfonate 2% w
Sodium Lignin Sulphonate 2%
Synthetic amorphous silica 3%
Kaolin 13%
The mixed ingredients are ground in a hammer mill into particles smaller than 100 m and 14 krons in diameter, then mixed again, sieved through sieve No. 50 and packed.
The compounds of formula I have strong herbicidal properties and have a wide range <sup>5</sup> according to the invention, they can be used to completely combat vegetation before and / or after emergence in squares where vegetation is not desired, e.g. around fuel tanks, ammunition storage, industrial storage areas<sup>10</sup> Poorly, next to oil sources, notice boards, highways and on railroad tracks. By choosing the right amount and duration of their application, you can use them to have a positive effect on plant development, and selectively control weeds in crops such as wheat and barley.
The exact amounts in which the compounds of formula I are used depend on the intended result, the amount of foliage, the type of weed to be controlled<sup>20</sup> ne, type of crop, soil type, type of agent used, method of application, climatic conditions etc. Because such a large number of factors play a role here, it is impossible to provide the amount of active substance suitable for <sup>25</sup> different situations, but generally speaking substar<sup>and </sup>these are used in an amount of 0.005-20 kg / ha, preferably 0.125-10 kg / ha. Higher amounts are usually used under unfavorable conditions, or when there is a longer presence of the agent in the soil, and ** smaller amounts are used for selective weed control in crops.
The compounds of formula I can be used in combination with known herbicides to selectively control weeds in crops <sup>35</sup> fine grain plants such as wheat and barley. Examples of such known herbicides are: chlorotoluron, i.e. 3- (3-chloro-4-methylphenyl) -1,1-dimethyl ylomocanik, MCPP, i.e. (±) 2- (4-chloro-2-methylphenoxy) acid - pro<sup>40</sup> vertical, methoxuron, i.e. 3- (3-chloro-4-methoxyphenyl) -, 1-dimethyl urea, metabenzothiozurom, i.e. 1- (benzothiazolyl-2 / -1, 3-dimethylmocnik, dichlofop, it is 2 - [/ 2,4-dichlorophenoxy / phenoxy] proprionic acid methyl ester, triallate, <sup>45</sup> this is S-2,3-dichloroToallyl diisopropylthiocarbamate, isoproturon, i.e. 3- (4-isopropylphenyl) -1,1-dimethylurea, or dipenzoate, i.e. 1,2-dimethyl-3,5-diphenylpyrazolium ion.
The compounds of formula (I) are preferably used together with known herbicidal compounds, especially with urea derivatives such as 3- / 3,4-dichlorophenyl / -1,1-dimethyl urea, 3- / 3,4-dichlorophenylZ-1-methoxy- 1-methylurea and 1,1-dimethyl-3- (a), o<sub>></sub>and<sup>j</sup>trifluoro-m-tolyl / urea, and also with triazine derivatives such as 2-chloro-4 - ethylamino / -6- (isopropylamino) -s-triazine, with uracil derivatives such as 5-bromo-3 -II tert. butyl-6-methyluracil, as well as with compounds such as N- / phosphonomethyl / glycine, 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4 (1H, 3H) -dione, N, N -dimethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid and related compounds, 4-chloro-2-butynyl 3-chlorophenylcarbamate, diisopropylthiocarbamic acid, S- (2,3,3-trichloroallyl ester), acid ethyl ester
126 541
N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionic, 4-amino-6-tert-butyl-3- (methylthio) -1,2,1,
4-triiazin-5- / 4H / -one, 2,2-dioxide 3-isopropyl-1H-2,3-benz »thyiodiazin- / 3H / -one-4, a, a,« - trifluoro-2 , 6-dinitro-N, N-dipropyl-p-toluidine, 1,1'-dimethyl-4,4'-di-pyridinium ion, monosodium methanarsonate and 2-chloro-2<sup>,</sup>6 '^ toetoksymetyloZ-diethyl-acetanilide.
The activity of the agents according to the invention was tested in • numerous tests carried out in greenhouses and in fields. These tests and their results are described below. In compiling the results, a numerical scale was used in which 0 means no effect and 10 means the strongest effect, as well as letter symbols with the following dip:
C - chlorosis or necrosis,
D - leaf loss,
E - suppression of rising,
G - growth retardation, '
H - zonal growth
U - incorrect coloration,
6Y drooping buds or flowers
Test A. Seeds of blood burner (Digitaria spp.), Single-weed weed (Echinochloa crus gaili), deaf Oats (Avena fatua), Cassia (Cassia tora), morning glory (Ipomoea ąpp). turnip (Xanthium spp.), sorghum, maize, soybean, rice and wheat, and tubers of cyprus (Cyperus rotundus) were placed in growth medium and treated before the emergence of the plants listed in Table 2 with compounds in solution in a non-phytotoxic solvent.
Comparative tests with seeds or tubers of the above-mentioned weeds and crops were prepared separately, without exposing them to the action of solvent or test compounds. In parallel, cotton plants in the 5-leaf stage (including cotyledons), bushy beans in the third-leaf stage, two-leaf burner, two-leaf weeds, deaf two-leaf oats, three-leaf cassia (together with cotyledons), morning glory leaves / including cotyledons), four-leaf turnips (including cotyledons), sorghum and four-leaf maize, two soy cotyledons, three-leaf rice, Single-leaf wheat and three-leaf cyprus plants were sprayed with solutions of the compounds listed in Table 2 in a non-phytotoxic solvent, and other groups of the same plants were sprayed with the solvent only, in order to obtain a comparative test.
Plants treated before and after emergence and plants in comparative trials were kept in the greenhouse for 16 days, after which all plants treated with test compounds were compared with the corresponding plants in the control samples and the reaction of the plants to their treatment was visually determined. The results given in Table 2 show that the compounds of formula 1 are very herbicidal.
Table 2
Test compound and its quantity kg / ha
<td rowspan="2">. Tested plant</td><td colspan="2">model 39</td><td>formula 40</td><td>formula 41</td><td>formula 42</td><td>formula 43</td><td>formula 44</td>
<td> 0,4</td><td> 2,0</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 2</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td><td> 8</td>
<td>After the emergence of plants Bushy beans</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>5C 10D</td>
<td>Cotton</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>5U 5C 9G</td><td>5C 9G</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>5C 9G</td>
<td>cocklebur</td><td>10C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Kas me</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td> —</td><td>9C</td><td>9C</td>
<td>cyprus</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td><td>9C</td><td>9C</td><td>9C</td>
<td>crabgrass</td><td>9C</td><td>'9C</td><td>5C 9G</td><td>5C 8G</td><td>10C</td><td>'9C</td><td>9C</td>
<td>Single sided weed</td><td>10C</td><td>10C</td><td>9C</td><td>9C</td><td>10C</td><td>10C</td><td>9C</td>
<td>Deaf oats</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td><td>4C 7G</td><td>9C</td>
<td>Wheat</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td><td>3C 7G</td><td>16C</td>
<td>Maize</td><td>9C</td><td>9C</td><td>10C</td><td>9C</td><td>10C</td><td>10C</td><td>5U 9C</td>
<td>Soy</td><td>9C</td><td>5C 9G</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Rice</td><td>10C</td><td>10C</td><td>5C 9G</td><td>8C</td><td>10C</td><td>10C</td><td>9C</td>
<td>Sorghum</td><td>9C</td><td>10C</td><td>9C</td><td>9C</td><td>10C</td><td> , <sup>90</sup></td><td>9C</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9H</td><td>9G</td><td>9C</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>3G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9C</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>9G</td><td>10E</td>
<td>crabgrass</td><td>9G</td><td>9G</td><td>9H</td><td>9H</td><td>10E</td><td>9H</td><td>4C 9G</td>
<td>Single sided weed</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td>
126 541
cd table 2 and a
<td> 1</td><td> 2</td><td><sup>3</sup></td><td> 4</td><td> 5</td><td> 6</td><td> 1 <sup>7</sup></td><td> 1 <sup>8</sup></td>
<td>Deaf oats</td><td>3C 9H</td><td>3C 9H</td><td>9H</td><td>9H</td><td>9H</td><td>9G</td><td>9H</td>
<td>Wheat</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9G</td><td>9H</td>
<td>Maize</td><td>10E</td><td>10E</td><td>10E</td><td>9H</td><td>10E</td><td>9G</td><td>9G</td>
<td>Soy</td><td>9H</td><td>9H</td><td>9H</td><td>10E</td><td>9H</td><td>9H</td><td>9H</td>
<td>Rice</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>Sorghum</td><td>10E</td><td>10E</td><td>9H</td><td>9H</td><td>9H</td><td>9G</td><td>9H</td>
Table 2 cd
<td rowspan="2"></td><td>Formula 45</td><td>Formula 46</td><td>Formula 47</td><td>Formula 48</td><td>Formula 49</td>
<td> 2</td><td> °-<sup>4</sup></td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>6C 9G</td><td>3C, 8G, 6Y</td><td>9C</td><td>9C</td><td>9C</td>
<td>Cotton</td><td>3C 9G</td><td>3C, 9G</td><td>9C</td><td>9C</td><td>9C</td>
<td>Bindweed</td><td>5C 8G</td><td>3C, 9G</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>5C 9G</td><td>2C, 7G</td><td>10C</td><td>10C</td><td>10C</td>
<td>Cassia</td><td>3C 6G</td><td>2C</td><td>9C</td><td>10C</td><td>10C</td>
<td>cyprus</td><td>IC 8G</td><td>7G</td><td>9C</td><td>10C</td><td>10C</td>
<td>crabgrass</td><td>5C 8G</td><td>7G</td><td>2C, 6G</td><td>3C, 7G</td><td>2C</td>
<td>Single sided weed</td><td>9C</td><td>9C</td><td>10C</td><td>10C</td><td>2C, 9H</td>
<td>Deaf oats</td><td>2G</td><td>6C</td><td>2C, 6G</td><td>2C, 8G</td><td>2C, 5G</td>
<td>Wheat</td><td>5G</td><td>2C, 6G</td><td>3C, 6G</td><td>3C, 7G</td><td>IC</td>
<td>Maize</td><td>IC 8G</td><td>IC, 8G</td><td>2U, 9G</td><td>10C</td><td>3C, 9G</td>
<td>Soy</td><td>2C 8G</td><td>3C</td><td>10C</td><td>5C, 9G</td><td>3C, 9G</td>
<td>Rice <sup>λ</sup></td><td>3C 8G</td><td>3C, 8G</td><td>3C, 8G</td><td>3C, 8G</td><td>6G</td>
<td>Sorghum</td><td>2C 8G</td><td>2C, 8G</td><td>10C</td><td>9C</td><td>2H, 8G</td>
<td>Before leaving Bindweed</td><td>5C 9G</td><td> 0</td><td>9G</td><td>9C</td><td>9C</td>
<td>cocklebur</td><td>9G</td><td> —</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>9G</td><td> 0</td><td>4C, 8G</td><td>9C</td><td>5C, 9G</td>
<td>cyprus</td><td>10E</td><td> 0</td><td>10E</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>2C 8G</td><td>3G</td><td>2C, 5G</td><td>2C, 6G</td><td>4G</td>
<td>Single sided weed</td><td>2C 9H</td><td>2G</td><td>9H</td><td>10H</td><td>2C, 9G</td>
<td>Deaf oats</td><td>8G</td><td> 0</td><td>9G</td><td>5C, 9H</td><td>8H</td>
<td>Wheat</td><td>8G</td><td>4H</td><td>9G</td><td>9H</td><td>5G</td>
<td>Maize</td><td>9G</td><td>3G</td><td>2U, 9G</td><td>10H</td><td>9G</td>
<td>Soy</td><td>2C 8H</td><td> 0</td><td>9H</td><td>9H</td><td>9Ή</td>
<td>Rice</td><td>10E</td><td>8H</td><td>10E</td><td>10E</td><td>9H</td>
<td>Sorghum</td><td>9G</td><td>4G</td><td>9H</td><td>10H</td><td>9G</td>
Table 2 cd
<td rowspan="2"></td><td>Formula 50</td><td>Formula 51</td><td>Formula 52</td><td>Wizor 53</td><td>Formula 54</td><td>Formula 55</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td> 1</td><td> 2</td><td> 01</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>After the emergence of plants Bushy beans</td><td>9D, 9G</td><td>9D, 9G</td><td>9C</td><td>9C</td><td>5C, 8G, 6Y</td><td>6C, 6G, 6Y</td>
<td>Cotton</td><td>6C, 9G</td><td>7C, 9G</td><td>9C</td><td>9C</td><td>2C, 2H, 7G</td><td>2C, 2H, 7G</td>
<td>Bindweed</td><td>9C</td><td>10C</td><td>10C</td><td>10C</td><td>IC</td><td>2C, 8G</td>
<td>cocklebur</td><td>6C, 9G</td><td>9C</td><td>10C</td><td>10C</td><td>3C, 9G</td><td>4C, 9G</td>
<td>Cassia</td><td>5C, 8G</td><td>5C, 8G</td><td>10C</td><td>9C</td><td>5G</td><td>5G</td>
<td>cyprus</td><td>7G</td><td>8G</td><td>10C</td><td>9C</td><td>2G</td><td>7G</td>
<td>crabgrass</td><td>2A</td><td> 0</td><td>5C, 8G</td><td>2C, 5G</td><td>2C</td><td> 0</td>
126 541
Table 2 cd
<td>AND</td><td> 2</td><td> 3</td><td> 4</td><td><sup>5</sup> 1</td><td> « 1</td><td> 7</td>
<td>Single sided trowel</td><td>9C</td><td>5C, 9H</td><td>6C, 9H</td><td>2C, 8H</td><td>3C, 9H</td><td>3C, 9H</td>
<td>Deaf oats</td><td>2C</td><td>8G</td><td>2C, 6G</td><td>4G</td><td>1C</td><td>5G</td>
<td>Wheat</td><td>1C</td><td>5C, 8G</td><td>2C</td><td>IC</td><td>1C</td><td>3C</td>
<td>Maize</td><td>9H</td><td>5C, 9H</td><td>10C</td><td>9C</td><td>3U, 9G</td><td>2C, 9G</td>
<td>Soy</td><td>9C</td><td>3C, 9G</td><td>5C, 9G</td><td>6C, 9G</td><td>1H</td><td>2H, 5G</td>
<td>Rice</td><td>4C, 8G</td><td>5C, 9G</td><td>5C, 8G</td><td>1C, 7G</td><td>8G</td><td>2C, 9G</td>
<td>Sorghum</td><td>2C, 9G</td><td>3C, 9G</td><td>5C, 9G</td><td><sub>V</sub>2U, 9G</td><td>9G</td><td>2U, 9G</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9G</td><td>9C</td><td>5G</td><td><sup>8G</sup></td>
<td>cocklebur</td><td>9G</td><td>10E</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kas me</td><td>8G</td><td>9G</td><td>6C, 9G</td><td>6C, 9G</td><td>5G</td><td>7G</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>10E</td><td>9G</td><td>5G</td><td>7G</td>
<td>crabgrass</td><td> 0</td><td>'6G</td><td>2C, 6G</td><td>1C, 3G</td><td> 0</td><td> 0</td>
<td>Single sided weed</td><td>9H</td><td>9H</td><td>2C, 9H</td><td>4C, 9G</td><td>2C, 8G</td><td>2C, 9G</td>
<td>Oops deaf</td><td>8G</td><td>2C, 9H</td><td>9G</td><td>8H</td><td>6G</td><td>2C, 8G</td>
<td>Wheat</td><td>2G</td><td>9G</td><td>5G</td><td>1C, 2G</td><td>i2G</td><td>8G</td>
<td>Corn '</td><td>2C, 8G</td><td>2U, 9H</td><td>9G</td><td>3C, 9G</td><td>2C, 7G</td><td>2C, 8G</td>
<td>Soy</td><td>8H</td><td>9H</td><td>9H</td><td>9H</td><td>3G</td><td>IC, 3G</td>
<td>Rice</td><td>10E</td><td>10E</td><td>10E</td><td>9H</td><td>8G</td><td>9H</td>
<td>Sorghum</td><td>9G</td><td>9H</td><td>2C, 9G</td><td>2C, 9G</td><td>8G</td><td>2H, 8G</td>
Table 2 cd
<td rowspan="2"></td><td>Formula 56</td><td>Formula 57</td><td>Formula 58</td><td colspan="2">Model 59 Formula 60</td><td>Formula 61</td>
<td> 0,4</td><td> ,0.4</td><td> 0,4</td><td colspan="2"> . 0,4 1 0,4</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>6C, 8G, 6Y</td><td>5G, 8G, 6Y</td><td>5G, 8G, 6Y</td><td>6C, 8G, 6Y</td><td>9C</td><td>9C, 9G</td>
<td>Cotton</td><td>2C, 2H, 8G</td><td>2C, 2H, 8G</td><td>3C, 3H, 9G</td><td>2H, 3C, 8G</td><td>9C</td><td>9C, 9G</td>
<td>Bindweed</td><td>1C, 8G</td><td>3C, 7G</td><td>9C</td><td>6C, 9G</td><td>Lioce</td><td>IjOC</td>
<td>cocklebur</td><td>2C, 9G</td><td>5C, 9G</td><td>9C</td><td>3C, 9G</td><td>Ilocano</td><td>10C</td>
<td>Cassia</td><td>5G</td><td>2C, 5G</td><td>IC</td><td>3C</td><td>9C</td><td>9C</td>
<td>cyprus</td><td><sup>30</sup></td><td>2G</td><td>IC, 5G</td><td>2G</td><td>10C</td><td>6C, 9G</td>
<td>crabgrass</td><td>3G</td><td> , 0</td><td>IC, 5G</td><td> .6</td><td>2C, 6G</td><td>3G</td>
<td>Single sided trowel</td><td>c</td><td>2H</td><td>5C, 9H</td><td>3C, 8H</td><td>3C, 9H</td><td>ec, 9H</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td>2C, 5G</td><td> 0</td><td>9G</td><td>3C, 9G</td>
<td>Wheat</td><td> 0</td><td> 0</td><td>lic</td><td> 0</td><td>IC, 2G</td><td>3C, 5G</td>
<td>Maize</td><td>6H</td><td>7H</td><td>7H</td><td>| 6H</td><td>6H</td><td>9H</td>
<td>Soy</td><td>7G</td><td>.6H</td><td>2H, 9G</td><td>2H, 8G</td><td>5C, 9G</td><td>4C, 9G</td>
<td>Rice</td><td>2G</td><td>6G</td><td>C</td><td>2G</td><td>5C, 9G</td><td>9C</td>
<td>Sorghum</td><td>7H</td><td>2C, 9G</td><td>8H</td><td>8G</td><td>3C, 9G</td><td>4C, 9G</td>
<td>Before leaving Bindweed</td><td>4G</td><td> 0</td><td>8G</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>5C, 9G</td><td>5C, 9G</td><td>8G</td><td>9C</td><td>9G</td><td>9H</td>
<td>Cassia</td><td>2C, 5G</td><td>3C, 7G</td><td>3G</td><td>2C</td><td>2C, 9G</td><td>3C, 9G</td>
<td>Gibora</td><td> 0</td><td>2G</td><td>SG</td><td> 0</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td> 0</td><td>2G</td><td> 0</td><td>about</td><td>5G</td><td>2C, 5G</td>
<td>One-sided weeds</td><td> 0</td><td> 0</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td>5G</td><td>S2G</td><td>9G</td><td>9G</td>
<td>Wheat</td><td> 0</td><td> 6</td><td>3G</td><td>2G</td><td>3G</td><td>8H</td>
<td>Maize</td><td>2G</td><td>4G</td><td>IC, 7G</td><td>IC, 7G</td><td>9H</td><td>2U, 9G</td>
<td>Soy</td><td>IC</td><td> 0</td><td>2C, 4H</td><td>ac</td><td>9H</td><td>9H</td>
<td>Rice</td><td> 0</td><td> 0</td><td>9H</td><td>5G</td><td>10E</td><td>10E</td>
<td>Sorghum</td><td>2H</td><td>3G</td><td>8G</td><td>8G</td><td>9H</td><td>9H</td>
126 541
Table 2 cd
<td rowspan="2"></td><td>Formula 62</td><td>Formula 63</td><td>Formula 64</td><td>Formula 65</td><td colspan="2">Model 66</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 9,4</td><td> 2 1</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>9C, 9G</td><td>5H, 8C</td><td>5C, 9H</td><td>8H, 9G</td><td>3C, 9G, 9D</td><td>3C, 9G, 9D</td>
<td>Cotton</td><td>7C, 9G</td><td>9C</td><td>10C</td><td>9C</td><td>9C</td><td>4C, 9G</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>9C</td><td>10C</td><td>10C</td><td>9C</td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>9C</td><td>9C</td>
<td>Cassia</td><td>6C, 9G</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>3C, 7G</td>
<td>cyprus</td><td>10C</td><td>9C</td><td>9C</td><td>9C</td><td><sup>9C</sup></td><td>2C, 6G</td>
<td>crabgrass</td><td>1C</td><td>6C</td><td>3U, 5G</td><td>6G</td><td>4C, 7G</td><td>2C, 6G</td>
<td>Single sided weed</td><td>3G</td><td>9C</td><td>10C</td><td>8C</td><td>10C</td><td>9C</td>
<td>Deaf oats</td><td> 0</td><td>6C</td><td>3C, 7G</td><td>2C</td><td>9C</td><td>2C, 5G</td>
<td>Wheat,</td><td> 0</td><td>3G, 4H</td><td>3C, 8G</td><td>2C</td><td>9C</td><td>1C, 4G</td>
<td>Maize</td><td>9H</td><td>5U, 8G</td><td>9C</td><td>5H, 7G</td><td>9C</td><td>2U, 8H</td>
<td>Soy</td><td>5C, 9G</td><td>6H, 8G</td><td>5Ή, 9G</td><td>5H, 8G</td><td>6C, 9G</td><td>6C, 9G</td>
<td>Rice</td><td>2C, 9G</td><td>7C</td><td>8C</td><td>8C</td><td>9C</td><td>6C, 8G</td>
<td>Sorghum</td><td>8H</td><td>9C</td><td>10C</td><td>2H, 7G</td><td>9C</td><td>3C, 8G</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9H</td><td>8H, 9G</td><td>5C, 9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>5H, 9G</td><td>8H, 9G</td><td>8H, 9G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>5C, 9G</td><td>5H, 8G</td><td>8H, 9G</td><td>8H<sub>r</sub> 8G</td><td>9C</td><td>9G</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>J.0E</td><td>9E, 9G</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>1C</td><td>8G</td><td>8G</td><td>7G</td><td>7G</td><td>8G</td>
<td>Single sided weed</td><td>2C, 8H</td><td>5H, 9G</td><td>5H, 9G</td><td>5H, 9G</td><td>9H</td><td><sub>t</sub> 9H</td>
<td>Deaf oats</td><td>8G</td><td>7G</td><td>8G</td><td>8G</td><td>8G</td><td>7G</td>
<td>Wheat</td><td>1C</td><td>7G</td><td>9G</td><td>7G</td><td>9G</td><td>9G</td>
<td>Maize</td><td>2C, 9H</td><td>5H, 9G</td><td>7H, 9G</td><td>7H, 9G</td><td>9G</td><td>2C, 9G</td>
<td>Soy</td><td>9H</td><td>6H, 8G</td><td>8H, 9G</td><td>7H, 8G</td><td>9H</td><td>7H</td>
<td>Rice</td><td>ilOE</td><td>10E</td><td>10E</td><td>7E, 8G</td><td>10E</td><td>10E</td>
<td>Sorghum</td><td>9H</td><td>5H, 9G</td><td>8H, 9G</td><td>7H, 9G</td><td>9H</td><td>9H</td>
Table 2 cd
<td rowspan="2"></td><td colspan="2">Pattern 67</td><td>Model 68</td><td>Model 69</td><td colspan="2">Visor 70</td>
<td> 2</td><td> 0,4</td><td> 2</td><td> 0,4</td><td> 2</td><td> 2</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>After the emergence of plants Bushy beans</td><td>3C, 9G, 10D</td><td>3C, 9G, 9D</td><td>9G, 10D</td><td>3C, 9G, 9D</td><td>5H, 8G, 6F</td><td>1C</td>
<td>Cotton</td><td>5C, 9G</td><td>5C, 9G</td><td>9C</td><td>9C</td><td>4C, 7G</td><td></td>
<td>Bindweed</td><td>10C</td><td>9C</td><td>10C</td><td>ICC</td><td>4G</td><td> 6</td>
<td>cocklebur</td><td>lflC</td><td>9C</td><td>9C</td><td>9C</td><td>8C</td><td> 0</td>
<td>Cassia</td><td>9C</td><td>3C, 7G</td><td>9C</td><td>9C</td><td>3C, 8G</td><td> 0</td>
<td>cyprus</td><td>9C</td><td>2C, 7G</td><td>9C</td><td>9C</td><td>8C</td><td> 0</td>
<td>crabgrass</td><td>5C, 8G</td><td>3G</td><td>9C</td><td>4C, 7G</td><td>5G</td><td> 0</td>
<td>Single sided weed</td><td>19C</td><td>10C</td><td>10C</td><td>10C</td><td>8C</td><td>1H</td>
<td>Deaf oats</td><td>4C, 8G</td><td>8G</td><td>9C</td><td>9C</td><td>4C</td><td> 0</td>
<td>Wheat</td><td>8C</td><td>4C, 8G</td><td>9C</td><td>9C</td><td>4C</td><td> 0</td>
<td>Maize</td><td>9C</td><td>5C, 9G</td><td>9C</td><td>9C</td><td>3H, 8G</td><td> 0</td>
<td>Soy</td><td>9C</td><td>4C, 8G</td><td>6C, 9G</td><td>6C, 9G</td><td>6H, 9G</td><td>1C</td>
<td>Rice</td><td>8C</td><td>5C, 8G</td><td>9C</td><td>9C</td><td>9C</td><td>3G</td>
<td>Sorghum</td><td>9C</td><td>2C, 8G</td><td>night</td><td>9C</td><td>3H, 8G</td><td>1C, 5G</td>
126 541
Table 2 cd
<td> 1</td><td> 2</td><td> 3</td><td> 1 <sup>4</sup></td><td> 5</td><td> 1 6</td><td> 1 <sup>7</sup></td>
<td>Before leaving Bindweed</td><td>5C, 9H</td><td>9G</td><td>10E</td><td>10E</td><td>7G</td><td>1C</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>5H, 8G</td><td>1C</td>
<td>Kas me</td><td>3C, 9G</td><td>9G</td><td>9G</td><td>9G</td><td>5H, 8G</td><td>1C</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>, 10E</td><td>10E</td><td>ljOE</td><td> 0</td>
<td>crabgrass</td><td>3C, 9G</td><td>7G</td><td>9H</td><td>3C, 9G</td><td>'2G</td><td> 0</td>
<td>Single sided weed</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>5H, 8G</td><td> 0</td>
<td>Deaf oats</td><td>3C, 9G</td><td>2C, 8G</td><td>2C, 9G</td><td>9G</td><td>5H, 7G</td><td> 0</td>
<td>Wheat</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>5H, 8G</td><td> 0</td>
<td>Maize</td><td>9G</td><td>9G</td><td>10E</td><td>10E</td><td>5H, 9G</td><td>3G</td>
<td>Soy</td><td>9H</td><td>9Ή</td><td>9H</td><td>9H</td><td>5H, 8G</td><td>1C</td>
<td>Rice</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>8H, '9G</td><td><sub>K</sub> 0</td>
<td>Sorghum</td><td>9H</td><td>9H</td><td>χΟΗ</td><td>9H</td><td>5H, 8G</td><td> 0</td>
Table 2 cd
<td rowspan="2"></td><td colspan="4">Formula 71</td><td>Formula 72</td><td>Formula 73</td><td>Formula 74</td>
<td> 10</td><td> 2</td><td><sup>2</sup> 1</td><td> | 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>2C, 2H</td><td>Λ0</td><td> , 0</td><td> 0</td><td>8C</td><td>9C</td><td>9C</td>
<td>Cotton</td><td></td><td></td><td> 0</td><td>about:</td><td>6C, 9G</td><td>5C, 9G</td><td>5C, 9G</td>
<td>Bindweed</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>10C</td><td>9C</td><td>5C, 9G</td>
<td>cocklebur</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>9C</td><td>5C, 9G</td><td>6G</td>
<td>Kas me</td><td> 0</td><td>1C</td><td> 0</td><td> 0</td><td>5C, 7G</td><td>5C, 9G</td><td>9C</td>
<td>cyprus</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>7G</td><td>3C, 8G</td><td>4G</td>
<td>crabgrass</td><td> 0</td><td> 0</td><td> 0</td><td>2G</td><td>1C</td><td>2G, 8G</td><td>3G</td>
<td>Single sided weed</td><td>2G</td><td> 0</td><td> 0</td><td>1C, 2H</td><td>1C, 7G</td><td>9C</td><td>2G</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>1C</td><td>7C</td><td> 0</td>
<td>Wheat</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>1C</td><td>7C</td><td>2G</td>
<td>Maize</td><td> 0</td><td> 0</td><td> 0</td><td> 0 !</td><td>3U, 8G</td><td>5U, 9C</td><td>8G</td>
<td>Soy</td><td>c</td><td> 0</td><td> 0</td><td> 0</td><td>9C</td><td>9C</td><td>9C</td>
<td>Rice</td><td>5G</td><td> 0</td><td> 0</td><td> 0</td><td>3C, 7G</td><td>5C, 8G</td><td>2C, 5G</td>
<td>Sorghum</td><td>3G</td><td> 0</td><td> 0</td><td> 0</td><td>8G</td><td>9C</td><td>1C, 9G</td>
<td>Before leaving Bindweed</td><td>7G</td><td>1C</td><td> 0</td><td> 0</td><td>9G</td><td>9G</td><td>8G</td>
<td>cocklebur</td><td>9G</td><td> 0</td><td> 0</td><td> 0</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>1C, 5G</td><td>1C</td><td> 0</td><td> 0</td><td>8G</td><td>9G</td><td>9G</td>
<td>cyprus</td><td>9G</td><td>9G</td><td> 0</td><td> 0</td><td>9G</td><td>10E</td><td>2G</td>
<td>crabgrass</td><td>1C</td><td> 0</td><td> 0</td><td> 0</td><td>6G</td><td>4C, 9G</td><td>5G</td>
<td>Single sided weed</td><td>1C, 3G</td><td> 0</td><td> 0</td><td> 0</td><td>9H</td><td>9H</td><td>5G</td>
<td>Deaf oats</td><td>1C, 5G</td><td> 0</td><td> 0</td><td> 0</td><td>4G</td><td>2C, 8G</td><td>2G</td>
<td>Wheat</td><td>2C, 7G</td><td>3G</td><td> 0</td><td> 0</td><td>4G</td><td>9H</td><td> 0</td>
<td>Maize</td><td>8G</td><td>3G</td><td> 0</td><td> 0</td><td>2C, 7G</td><td>10E</td><td>2C, 7G</td>
<td>Soy</td><td>4G</td><td> 0</td><td> 0</td><td> 0</td><td>9H</td><td>9H</td><td>2C, 4H</td>
<td>Rice</td><td>2C, 7G</td><td> 0</td><td> 0</td><td> 0</td><td>9H</td><td>10E</td><td>2C, 5G</td>
<td>Sorghum</td><td>5G</td><td> 0</td><td> 0</td><td> ° 1</td><td>1C, 9G</td><td>10E</td><td>8G</td>
Table 2 cd
<td rowspan="2"></td><td>Formula 75</td><td>Formula 76</td><td>Model 77</td><td>Model 78</td><td>Style 79</td><td>Style 80</td>
<td> 0,4</td><td>j0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>After the emergence of plants Bushy beans</td><td>9C</td><td>10D</td><td>9C</td><td>9C</td><td>4C, 9G, 6Y</td><td>3C, 5G, 6Y</td>
<td>Cotton</td><td>9C</td><td>3C, 9G</td><td>5C, 9G</td><td>5C, 9G</td><td>2C, 3H</td><td>IC</td>
128 541
Table 2 cd
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>Bindweed</td><td>y> c</td><td>, 10C</td><td>9C</td><td>10C</td><td>3C, 8G</td><td> 0</td>
<td>cocklebur</td><td>9C</td><td>5C, 9G</td><td>3H, 9G</td><td>10C</td><td>3C, 8G</td><td>5C</td>
<td>Kas me</td><td>9C</td><td>3C, 8G</td><td>9C</td><td>9C</td><td>2C</td><td> 0</td>
<td>cyprus</td><td>2C, 6G</td><td>2C, 9G</td><td>6C, 9G</td><td>6C, 9G</td><td>6G</td><td> 0</td>
<td>crabgrass</td><td>3C, 8G</td><td>5C, 8G</td><td>9C</td><td>2C, 6G</td><td>2G</td><td>2C</td>
<td>Single sided weed</td><td>10C</td><td>9C</td><td>5C, 8H</td><td>9C</td><td>7H</td><td>2C, 6G</td>
<td>Deaf oats</td><td>9C</td><td>5C, 7G</td><td><sub>L</sub> 0</td><td>9C</td><td> 1°</td><td>1C</td>
<td>Wheat</td><td>9C</td><td>'3C, 8G</td><td> 0</td><td>9C</td><td> 0</td><td>2G</td>
<td>Maize</td><td>5U, 8G</td><td>9H</td><td>9C</td><td>9C</td><td>2G</td><td>1C, 7G</td>
<td>Soy</td><td>8C</td><td>2C, 9G</td><td>5C, 9G</td><td>9C</td><td>5C, 7G</td><td>1C, 5G</td>
<td>Rice</td><td>8C</td><td>5C, 9G</td><td>9C</td><td>9C</td><td>BC</td><td>2C, 4G</td>
<td>Sorghum</td><td>5C, 9G</td><td>3U, 9G</td><td>2C, 9G</td><td>9C</td><td>, 5G</td><td>2C, 7G</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>8G</td><td>3G</td>
<td>Rizepień</td><td>9G</td><td>9G</td><td><X0E</td><td>9G</td><td>8G</td><td></td>
<td>Cassia</td><td>9C</td><td>9G</td><td>9G</td><td>9G</td><td> 0</td><td> 0</td>
<td>cyprus</td><td>10E</td><td>9G</td><td>10E</td><td>11 OE</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>2C, 9G</td><td>2C, 9G</td><td>5G</td><td>9H</td><td>2G</td><td>2G</td>
<td>Single sided weed</td><td>9H</td><td>5C, 9H</td><td>2C, 8G</td><td>9H</td><td>9G</td><td>1C, 8H</td>
<td>Deaf oats</td><td>1C, 8G</td><td>2C, 8H</td><td>2G</td><td>3C, 9G</td><td>4G</td><td> 0</td>
<td>Wheat</td><td>1C, 9H</td><td>9G</td><td> 0</td><td>9H</td><td>5G</td><td> 6</td>
<td>Maize</td><td>2C, 9H</td><td>9G</td><td> — .</td><td>10E</td><td>2C, 7G</td><td>JJC</td>
<td>Soy</td><td>9H</td><td>8H</td><td>9H</td><td>9H</td><td>1C, 5H</td><td> 0</td>
<td>Rice</td><td>10E</td><td>10E</td><td>9H</td><td>Ί0Ε</td><td>9H</td><td>8H</td>
<td>Sorghum</td><td>2C, 9H</td><td>9H</td><td>9G</td><td>ιΰΗ</td><td>2C, 9G</td><td>8G</td>
Table 2 cd
<td rowspan="2"></td><td>Model 81</td><td>Wfeór 82</td><td>Model 83</td><td>Formula 84</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td>
<td>After the emergence of plants Bushy beans</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Cotton</td><td>9C</td><td>9C</td><td>9C</td><td>5C, 9G</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>9C</td><td>10C</td><td>9C</td><td>9C</td>
<td>Kas me</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td>
<td>cyprus</td><td>2C, 8G</td><td>7G</td><td>4G</td><td>7G</td>
<td>crabgrass</td><td>2C, 8G</td><td>9G</td><td>1C, 5G</td><td>9C</td>
<td>Single sided weed</td><td>5C, 9H</td><td>6C, 9H</td><td>6C, 9H</td><td>9C</td>
<td>Deaf oats</td><td>1C, 8G</td><td>2C, 7G</td><td>4G</td><td>3C, 7G</td>
<td>Wheat</td><td>1C, 7G</td><td>2C, 6G</td><td>2G</td><td>3C, 6G</td>
<td>Maize</td><td>10C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Soy</td><td>2C, 8G</td><td>9C</td><td>5C, 9G</td><td> —</td>
<td>Rice</td><td>3C, 8G</td><td>5C, 8G</td><td>5C, 9G</td><td> —</td>
<td>Sorghum</td><td>2C, 8G</td><td>2C, 8G</td><td>1C, 8G</td><td>5C, 9G</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>3C, 9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kas me</td><td>9G</td><td>9G</td><td>8G</td><td>10E</td>
<td>cyprus</td><td>8G</td><td>9G</td><td>7G</td><td>10E</td>
<td>crabgrass</td><td>2C, 9G</td><td>1C, 8G</td><td>5G</td><td>2C, 9G</td>
126 541
Table 2 cd
<td> 1</td><td colspan="2"> 2 [ 3</td><td> 4</td><td> 5</td>
<td>Single sided weed</td><td>9H</td><td>2C, 9H</td><td>9H</td><td>> 9H</td>
<td>Deaf oats</td><td>IC, 7G</td><td>IC, 8G</td><td>7G</td><td>9Ή</td>
<td>Wheat</td><td>IC, 5G</td><td>7G</td><td>5G</td><td>9H</td>
<td>Maize</td><td>IC, 9G</td><td>2C, 9G</td><td>1U, 9G</td><td>9H</td>
<td>Soy</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td>
<td>Rice</td><td>10E</td><td>10E</td><td>9H</td><td>10E</td>
<td>Sorghum</td><td>2C, 9G</td><td>9H</td><td>IC, 9G</td><td>9H</td>
Table 2 cd
<td rowspan="2"></td><td>Formula 85</td><td>Model 86</td><td>Model 87</td><td>Model 88</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>9C</td><td>9C</td><td>5C, 8G, 6Y</td><td>9C</td>
<td>Cotton</td><td>6C, 9G</td><td>4C, 9G</td><td>5C, 9G</td><td>9C</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>9C</td><td>9C</td>
<td>cocklebur</td><td>10C</td><td>9C</td><td>5C, 9G</td><td>10C</td>
<td>Cassia</td><td>9C</td><td>5C, 9G</td><td>5C, 9G</td><td>5C, 9G</td>
<td>cyprus</td><td>IC, 8G</td><td>2C, 8G</td><td> 0</td><td>8G</td>
<td>crabgrass</td><td>3G</td><td>2C, 6G</td><td>5C, 8G</td><td>4G</td>
<td>Single sided weed</td><td>9C</td><td>3C, 9H</td><td>3C, 7H</td><td>9C</td>
<td>Deaf oats</td><td>IC, 2G</td><td>3G</td><td>2C</td><td>IC, 2G</td>
<td>Wheat</td><td>IC, 4G</td><td>2G</td><td> 0</td><td>IC, 2G</td>
<td>Maize</td><td>9C</td><td>3U, 8G</td><td>8U, 9G</td><td>5U, 9H</td>
<td>Soy</td><td>9C</td><td>5C, 9G</td><td>5C, 8G</td><td>9C</td>
<td>Rice</td><td> —</td><td>3C, 7G</td><td>3C, 8G</td><td>3C, 8G</td>
<td>Sorghum</td><td>5C, 9G</td><td>2C, 8G</td><td>2C, 9G</td><td>8G</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>8G</td><td>9G</td><td>8G</td><td>9G</td>
<td>Cassia</td><td>8G</td><td>8G</td><td>8G</td><td>3C, 8G</td>
<td>cyprus</td><td>5G</td><td>2C, 9G</td><td>9C</td><td>10E</td>
<td>crabgrass</td><td> 0</td><td>2C, 8G</td><td>2C, 8H</td><td>2C, 8G</td>
<td>Single sided weed</td><td>9H</td><td>2C, 9H</td><td>2C, 9H</td><td>5C, 9H</td>
<td>Deaf oats</td><td>5G</td><td>2C, 8G</td><td>4G</td><td>IC, 8G</td>
<td>Wheat</td><td>3G</td><td>4G</td><td> 0</td><td>9H</td>
<td>Maize</td><td>8G</td><td>9G</td><td>2C, 8G</td><td>9G</td>
<td>Soy</td><td>9H</td><td>9H</td><td>7H</td><td>9H</td>
<td>Rice</td><td>9H</td><td>9H</td><td>9H</td><td>10E</td>
<td>Sorghum</td><td>2C, 9G</td><td>9H</td><td>IC, 9G</td><td>5C, 9H</td>
Table 2 cd
<td rowspan="2"></td><td>Model 89</td><td>90's</td><td>Model 91</td><td>Formula 92</td><td>Formula 93</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td>
<td>After the emergence of plants Bushy beans</td><td><sup>9C</sup></td><td>6C, 9G</td><td>9C</td><td>10D, 9G</td><td>9C</td>
<td>Cotton</td><td>2C, 2H, 5G</td><td>4C, 9G</td><td>9C</td><td>6C, 9G</td><td>10C</td>
<td>Bindweed</td><td>9C</td><td>10C</td><td>10C</td><td>10C</td><td>l 0C</td>
<td>cocklebur</td><td>9C</td><td>9C</td><td>9C</td><td>5C, 9G</td><td>9C</td>
<td>Cassia</td><td>9C</td><td>9C</td><td>6C, 9G</td><td>9C</td><td>9C</td>
<td>cyprus</td><td>9G</td><td>9C</td><td>6C, 9G</td><td>7C, 9G</td><td>10C</td>
126 541
Table 2 cd
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td>
<td>crabgrass</td><td>5C, 8H</td><td>10C</td><td>4C, 8H</td><td>5C, 8G</td><td>9C</td>
<td>Single sided weed</td><td>6C, 9H</td><td>9C</td><td>9C</td><td>10C</td><td>9C</td>
<td>Deaf oats</td><td>4C, 8G</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Wheat</td><td>2C, 8G</td><td>6C, 8G</td><td>9C</td><td>9C</td><td>9C</td>
<td>Maize</td><td>2C, 9H</td><td>5U, 9C</td><td>10C</td><td>9C</td><td>10C</td>
<td>Soy</td><td>2C, 8G</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Rice</td><td>3C, 8G</td><td>3C, 9G</td><td>6C, 8G</td><td>9C</td><td>5C, 9G</td>
<td>Sorghum</td><td>2U, 9G</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td>
<td>Before leaving Bindweed</td><td>9G</td><td>ap</td><td>9G</td><td>9G</td><td>10E</td>
<td>cocklebur</td><td>9G</td><td>8G</td><td>8G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cyprus -</td><td>IC, 9G</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>2C, 9G</td><td>9H</td><td>3C, 9G</td><td>2C, 9G</td><td>IC, 9G</td>
<td>Single sided weed</td><td>ec> 9H</td><td>9H</td><td>9H</td><td>9H</td><td>IC, 9H</td>
<td>Deaf oats</td><td>2C, 8G</td><td>2C, 8G</td><td>3C</td><td>2C, 9G</td><td>2C, 9H</td>
<td>Wheat</td><td>9G</td><td><sup>9H</sup></td><td>9H</td><td>9H</td><td>9H</td>
<td>Maize</td><td>2C, 8G</td><td>9H</td><td>IC, 9G</td><td>9H</td><td>fOE</td>
<td>Soy</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td>
<td>Rice</td><td>9H</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>Sorghum</td><td>4C, 9H</td><td>9H</td><td>5C, 9H</td><td>9H</td><td>10E</td>
and
Table 2 cd
<td rowspan="2"></td><td>Formula 94</td><td>Formula 95</td><td>Template 96</td><td>Visor 97</td><td>Wizor 98</td><td>Visor 99</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>After the emergence of plants Bushy beans</td><td>8C, 9G</td><td>9G</td><td>9C</td><td>9C</td><td>4C, 7G, 6G</td><td>9C</td>
<td>Cotton</td><td>6C, 9G</td><td>6C, 9G</td><td>2C, 3H, 8G</td><td>2C, 3H, 9G</td><td>2C</td><td>9C</td>
<td>Bindweed</td><td>9C</td><td>9C</td><td>2C, 8G</td><td>5C, 9G</td><td>2C</td><td>10C</td>
<td>cocklebur</td><td>2H, 8G</td><td>5C, 9G</td><td>2C</td><td>3C, 8G</td><td>2C, 5G</td><td>9C</td>
<td>Cassia</td><td>5C, 9G</td><td>9C</td><td>IC, 6H</td><td>9C</td><td>IC</td><td>9C</td>
<td>cyprus</td><td>9G</td><td>9C</td><td>8G</td><td>9C</td><td>IC, 5G</td><td>8G</td>
<td>crabgrass</td><td>2C, 6G</td><td>9C</td><td>IC, 5G</td><td>9C</td><td> 0</td><td>3C, 9G</td>
<td>Single sided weed</td><td>4C, 9H</td><td>9C</td><td>5C, 9H</td><td>9C</td><td>3C</td><td>ljOC</td>
<td>Deaf oats</td><td>2C, 6G</td><td>9C</td><td>IC, 7G</td><td>6C, 9G</td><td> 0</td><td>9C</td>
<td>Wheat</td><td>3C, 5G</td><td>9C</td><td>6G</td><td>5C, 8G</td><td> 0</td><td>9C</td>
<td>Maize</td><td>5U, 9G</td><td>9C</td><td>9H</td><td>9C</td><td>IC, 7H</td><td>9C <sup>4</sup></td>
<td>Soy</td><td>9C</td><td>9C</td><td>IC, 5H</td><td>8C</td><td>2C</td><td>9C</td>
<td>Rice</td><td>5C, 9G</td><td>9C</td><td>8G</td><td>8C</td><td>2C, 7G</td><td>10C</td>
<td>Sorghum</td><td>3C, 9H</td><td>9C</td><td>9G</td><td>9C</td><td>IC, 5G</td><td>10C</td>
<td>Before leaving Bindweed</td><td>9G</td><td>10E</td><td>9G</td><td>10E</td><td> 0</td><td>9G</td>
<td>Rzepdeń</td><td>8G</td><td>10E</td><td>Ipe</td><td>9G</td><td> 0</td><td>9G</td>
<td>Cassia</td><td>8G</td><td>3C, 9G</td><td>2C, 8G</td><td>8G</td><td> 0</td><td>8G</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>Λ0Ε</td><td>10E</td><td>10E</td><td>Loe</td>
<td>crabgrass</td><td>2C, 5H</td><td>5C, 9G</td><td>2C, 8G</td><td>5C, 9G</td><td> 0</td><td>2C, 9G</td>
<td>Single sided weed</td><td>9H</td><td>5C, 9H</td><td>3C, 9H</td><td>7C, 9H</td><td>2G</td><td>2C, 9H</td>
<td>Deaf oats</td><td>6G</td><td>5C, 9H</td><td>IC, 5G</td><td>4C, 6G</td><td> 0</td><td>2C, 7G</td>
<td>Wheat</td><td>6G</td><td>10E</td><td>2C, 9H</td><td>9H</td><td> 0</td><td>9H</td>
<td>Maize</td><td>8G</td><td>10H</td><td>9G</td><td>9H</td><td>IC, 4G</td><td>9G</td>
126 541
Table 2 cd
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>Soy</td><td>2C, 5G</td><td>9H</td><td>9H</td><td>9H</td><td> 0</td><td>9H</td>
<td>Rice</td><td>9H</td><td>IDE</td><td>10E</td><td>10E</td><td>8H</td><td>10E</td>
<td>Sorghum</td><td>IC, 9G</td><td>10H</td><td>9H</td><td>9Ή</td><td>3G</td><td>9H</td>
Table 2 cd
<td rowspan="2"> < -</td><td>Formula 100</td><td>Model 101</td><td>Pattern, 102</td><td>Wizor 103</td><td>Formula 104</td><td>Formula 105</td>
<td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td><td> 0,4</td>
<td>After the emergence of plants Bushy beans</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>6C, 9G</td>
<td>Cotton</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>9C</td><td>10C</td>
<td>cocklebur</td><td>ipc</td><td>2C, 8G</td><td>9C</td><td>9C</td><td>9C</td><td>9C</td>
<td>Cassia</td><td>10C</td><td>3C, 8G</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td>
<td>cyprus</td><td>5C, 9G</td><td>IC, 8G</td><td>2C, 9G</td><td>10C</td><td>2C, 8G</td><td>9C</td>
<td>crabgrass</td><td>3G</td><td>9C</td><td>IC, 8G</td><td>5C, 8G</td><td>2C, 7G</td><td>9C</td>
<td>Single sided weed</td><td>6C, 9H</td><td>5C, 8H</td><td>9C</td><td>9C</td><td>9C</td><td>10C</td>
<td>Deaf oats</td><td>3C, 70</td><td>IC, 5G f '</td><td>4C, 7G</td><td>9C</td><td>3C, 7H</td><td>8C</td>
<td>Wheat</td><td>2C, 6G</td><td>IC</td><td>4C, 6G</td><td>5C, 8G</td><td>IC, 5H</td><td>8C</td>
<td>Maize</td><td>lpc</td><td>9C</td><td>9C</td><td>7U, 9C</td><td>9C</td><td>9C</td>
<td>Soy <sub>?</sub></td><td>6C, 9G</td><td>9C</td><td>8C</td><td>6C, 9G</td><td>9C</td><td>5C, 9G</td>
<td>Rice</td><td> —</td><td>5C, 9G</td><td>5C, 9G</td><td>9C</td><td>5C, 8G</td><td>6C, 9G</td>
<td>Sorghum</td><td>2C, 9G</td><td>3C, 9G</td><td>3C, 9G</td><td>9C</td><td>9C</td><td>9C</td>
<td>Before leaving Bindweed</td><td>9G</td><td>9G</td><td>9G</td><td>9H</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>8G</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cassia</td><td>9G</td><td>2C, 8G</td><td>9G</td><td>9G</td><td>9G</td><td>9G</td>
<td>cyprus</td><td>10E</td><td>IC, 9G</td><td>10E</td><td>10E</td><td>2C, 8G</td><td>10E</td>
<td>crabgrass</td><td>2G</td><td>IC, 5G</td><td>2C, 9G</td><td>5C, 9G</td><td>2C, 9G</td><td>IC, 9G</td>
<td>Single sided weed</td><td>2C, 9H</td><td>2C, 9H</td><td>4C, 9H</td><td>9H</td><td>2C, 9H</td><td>6C, 9H</td>
<td>Deaf oats</td><td>IC, 7G</td><td>2C, 8G</td><td>2C, 7G</td><td>4C, 9G</td><td>2Ć, 8G</td><td>5C, 8G</td>
<td>Wheat</td><td>6G</td><td>6G</td><td>9H</td><td>9H</td><td>IC, 6G</td><td>9H</td>
<td>Maize</td><td>2U, 9G</td><td>10H</td><td>9G</td><td>9G</td><td>1U, 9G</td><td>9H</td>
<td>Soy</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td>
<td>Rice</td><td>10E</td><td>10E</td><td>Loe</td><td>10E</td><td>10E</td><td>10E</td>
<td>Sorghum</td><td>2C, 9G</td><td>9H</td><td>9H</td><td>9H</td><td>9H</td><td>5C, 9H</td>
Attempts »B. <sup>M</sup>
Two troughs were filled with Fallsington's fertilized and calcareous dust and sandy soil. In one basin, maize, sorghum, panicle and several grass weeds were sown, and in the other<sup>M </sup>soybeans, cyprus tubers and several seeds, broad-leaved weeds. The following grass and broad-leaved weeds were planted: blooder (Digitaria sanguinalis), single-sided weed (Echinochloa crusgalli), deaf oats (Avena fatua), M wild sorghum (Sorghum halepense), trichinosis (Sataria faberia), dallis grass (Paspalum dilatatuim), rye plant, rye (Brassica arvensis), turnip (Xanthium pennsylvanicum), amaranth (Amaranthus retroflexus), morning glory (Ipomoea es hederacea), cassia (Cassia tora), mallow (Sida spinosa), Rosewood Avicenny (Abutilon theophrasti) and Datura strata (Datura istramonium). The smaller trough was also filled with prepared soil and rice and wheat were sown in it, and in another small trough 'sugar beet' was sown.
The four troughs described above were treated before the emergence of plants with solutions of the test compounds in non-phytotoxic solvents, namely, these solutions were sprayed on the soil surface before seed germination. Comparative tests were prepared in an analogous manner, in which the compounds of formula 1 were not used. After 28 days, the results were evaluated by comparison with control samples. The test results are given in Table 3.
126 541
8$
Table 3
<td></td><td></td><td>Test compound</td><td>and its quantity</td><td>kg / ha</td><td></td>
<td>Tested plant</td><td></td><td>Formula 39</td><td></td><td colspan="2">Formula 39</td>
<td> -</td><td> 1/128</td><td> 1 1/64</td><td> 1/32</td><td> 1/16</td><td>| l / 4<sup>;</sup></td>
<td>Bloody fingerstick</td><td>9G, 9C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Single sided weed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>Ilocano</td>
<td>Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>10E</td><td>10E</td>
<td>Deaf oats</td><td>8G, 8C</td><td>10C</td><td>10C</td><td>7G, 5C</td><td>8G, 8C</td>
<td>Wild Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Dallis grass</td><td>8G, 8C</td><td>10C</td><td>10C</td><td>, L0C</td><td>1 ° C</td>
<td>fretsaw</td><td>9G, 9C</td><td>10C</td><td>10C</td><td>night</td><td>10C</td>
<td>Kentucky bluegrass</td><td>10C</td><td>10E</td><td>10E</td><td>night</td><td>10C</td>
<td>brome</td><td>10C</td><td>10C</td><td>10C</td><td>Ilocano</td><td>10C</td>
<td>White beet</td><td>8G, 5H</td><td>10C</td><td>10C</td><td>iljoc</td><td>pour</td>
<td>Maize</td><td>10C</td><td>10C</td><td>10C</td><td>10E</td><td>. 10E</td>
<td>Mustard</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>1QC</td>
<td>cocklebur</td><td>7G, 5C</td><td>7G</td><td>8G</td><td>8G, 5H</td><td>, 8G, 8H</td>
<td>amaranth</td><td> — . ....</td><td> —</td><td> —</td><td>10E</td><td><sub>;</sub> 1OE</td>
<td>cyprus</td><td>10e</td><td><sup>10E</sup></td><td>10E</td><td>1OE</td><td></td>
<td>Cotton</td><td>7G</td><td>8G</td><td>8G, 5C</td><td>1OE</td><td>IN</td>
<td>Bindweed</td><td>7G</td><td>7G</td><td>8G, 6C</td><td>8G</td><td>8G, 8C</td>
<td>Cassia</td><td>8G, 8C</td><td>10C</td><td>10C</td><td>8G, 5C</td><td>8G, 8C</td>
<td>mallow</td><td> —</td><td> —</td><td> —</td><td>1 ° C</td><td>1 ° C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Datura stramonium</td><td>9G, 9C</td><td>9G, 9C</td><td>9G, 9C</td><td>8G</td><td>8G</td>
<td>Soy</td><td>8G</td><td>8G, 5C</td><td>10C</td><td>8G, 8C</td><td>8G, 8C</td>
<td>Rice</td><td>10C</td><td>10C</td><td>10E</td><td>10E</td><td>1OE</td>
<td>Wheat</td><td>10C</td><td>Ilocano</td><td>10C</td><td>9G, 9H</td><td>10H</td>
Table 3 cd
<td rowspan="2"></td><td colspan="3">Formula 40</td><td colspan="3">Formula 41</td>
<td> 1/64 <sup>r</sup></td><td> 1/32</td><td> 1/16</td><td> 1/64</td><td> 1/32</td><td> ,1/16</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> / 7</td>
<td>Bloody finger</td><td>8G, 3C</td><td>9G, 9C</td><td>10C</td><td>8G, 5C</td><td>8G, 5C</td><td>10C</td>
<td>Single sided weed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>9G, 9C</td><td>10C</td><td>10C</td>
<td>Deaf oats</td><td>8G, 8C</td><td>10C</td><td>9G, 9C</td><td>5G</td><td>7G, 5C</td><td>6G, 5C</td>
<td>Wild Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>9G, 9C</td><td>10C</td><td>10C</td>
<td>Dallis grass</td><td>in</td><td>10C</td><td>10C</td><td>5G</td><td>7G</td><td>8G, 8C</td>
<td>fretsaw</td><td>10C</td><td>10C</td><td>Ilocano</td><td>8G</td><td>9G, 9C</td><td>, 10C</td>
<td>Kentucky bluegrass</td><td>10C</td><td>10E</td><td>10E</td><td>10C</td><td>IOE</td><td>10E</td>
<td>brome</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>1 ° C</td>
<td>White beet</td><td>1 ° C</td><td>10C</td><td>10C</td><td>10C</td><td>1 ° C</td><td>1OC,</td>
<td>Maize</td><td>10C</td><td>10C</td><td>10C</td><td>7G, 3C</td><td>7G, 5C</td><td>10C</td>
<td>Mustard</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>, 10C</td><td>1 ° C</td>
<td>cocklebur</td><td>8G</td><td>8G, 5C</td><td>8G, 7C</td><td>7G</td><td>8G, 5C</td><td>8G, 7C</td>
<td>amaranth</td><td> —</td><td> —</td><td> —</td><td> —</td><td> —</td><td>y-</td>
<td>cyprus</td><td>IOE</td><td>NOE</td><td>10E</td><td>IOE</td><td>10E</td><td>IOE</td>
<td>Cotton</td><td>9G, 9C</td><td>10C</td><td>9G, 9C</td><td>7G</td><td>7G</td><td>7G</td>
<td>Bindweed</td><td>8G, 8C</td><td>10C</td><td>10C</td><td>8G, 8C</td><td>Ilocano</td><td>9G, 9C</td>
<td>Cassia</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>mallow</td><td> —</td><td> —</td><td> —</td><td> —</td><td> —</td><td> —</td>
<td>Avicenna</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Datura stramonium</td><td>9G, 9C</td><td>10C</td><td>1 ° C</td><td>10C</td><td>8G, 8C</td><td>10C</td>
126 541
Table 3 cd
<td> 1</td><td><sup>2</sup> 1</td><td><sup>3</sup> 1</td><td> 1 <sup>4</sup></td><td><sup>5</sup> 1</td><td> 1 <sup>6</sup> and</td><td> 1 <sup>7</sup></td>
<td>Soy</td><td>10C</td><td>9G, 9C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 5C</td>
<td>Rice</td><td>10E</td><td>10E</td><td>1OE</td><td>1 ° C</td><td>1 ° C</td><td>1OE</td>
<td>Wheat</td><td>8G, 8C</td><td>10C</td><td>10C</td><td>10C</td><td>8G, 8C</td><td>1 ° C</td>
Table 3 cd
<td></td><td></td><td>Formula 42</td><td></td><td></td><td>Formula 43</td><td></td>
<td></td><td> 1/64</td><td> 1/32</td><td>iV16</td><td> 1/64</td><td> 1 1/32</td><td> 1/16</td>
<td>Bloody fingerstick</td><td>7G, 3C</td><td>9G, 9C</td><td>, 10C</td><td>7G</td><td>8G 5C</td><td>1 ° C</td>
<td>Single sided weed</td><td>9G, 9C</td><td>10C</td><td>10C</td><td>3G</td><td>7G 7C</td><td>9G 9C</td>
<td>Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>7G</td><td>9G 8C</td><td>10C</td>
<td>Deaf oats</td><td>4G</td><td>5G, 3C</td><td>10C</td><td> 0</td><td>IOC</td><td>5G 3C</td>
<td>Wild Sorghum</td><td>7G, 7C</td><td>8G, 8C</td><td>10C</td><td>6G</td><td>7G 7C</td><td>8G 8C</td>
<td>Dallis grass</td><td> 0</td><td>4G, 3C</td><td>6G</td><td> 0</td><td> 0</td><td>3G. ·</td>
<td>fretsaw</td><td>7G, 3C</td><td>8G, 5C</td><td>ioc</td><td>6G 3C</td><td>5G 3C</td><td>8G 8C</td>
<td>Kentucky bluegrass</td><td>10C</td><td>8G, 8C</td><td>10E</td><td>7G 3C</td><td>8G 5C</td><td>10C</td>
<td>brome</td><td>7G</td><td>10E</td><td>10C</td><td>3G</td><td>3G</td><td>6G 3C</td>
<td>White beet</td><td>10C</td><td>10C</td><td>10C</td><td>IOC</td><td>10C</td><td>10C</td>
<td rowspan="2">Maize</td><td rowspan="2">7G, 5C</td><td></td><td></td><td></td><td></td><td></td>
<td>10C</td><td>10C</td><td>6G 5H</td><td>7G 5C</td><td>10C</td>
<td rowspan="2">Mustard</td><td rowspan="2">10C</td><td></td><td></td><td></td><td></td><td></td>
<td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>8G, 9C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G 3C</td><td>10C</td><td>8G 5C</td>
<td>amaranth</td><td> —</td><td> —</td><td> —</td><td> —</td><td> —</td><td></td>
<td>cyprus</td><td>7G</td><td>7G,</td><td>8G</td><td>7G</td><td>7G 3C</td><td>8G</td>
<td>Cotton</td><td>10C</td><td>8G, 5C</td><td>10C</td><td>10C</td><td>8G</td><td>9G 5C</td>
<td>Bindweed</td><td>8G, 8C</td><td>9G, 9C</td><td>10C</td><td>8G 8C</td><td>10C</td><td>1 ° C</td>
<td>Cassia</td><td>10C</td><td>10C</td><td>10C</td><td>IOC</td><td>10C</td><td>IOC</td>
<td>mallow</td><td> —</td><td> —</td><td> , —</td><td> —</td><td> —</td><td> _</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>7G 8C</td><td>8G 9C</td><td>10C</td>
<td rowspan="2">Datura stramonium</td><td rowspan="2">8G, 5C</td><td></td><td></td><td></td><td></td><td></td>
<td>9G, 8C</td><td>9G, 9C</td><td>9G 9C</td><td>Ilocano</td><td>10C</td>
<td>Soy</td><td>10C</td><td>8G, 5C</td><td>8G, 8C</td><td>8G 7C</td><td>9G 8C</td><td>8G 5C</td>
<td rowspan="2">Rice</td><td rowspan="2">8G, 8C</td><td></td><td></td><td></td><td></td><td></td>
<td>10C</td><td>ioc</td><td>, 6G 5C</td><td>8G 8C</td><td>10C</td>
<td>Wheat</td><td>3G</td><td>4G</td><td>5G</td><td> 0</td><td>2G;</td><td>4G 3C</td>
Table 3 cd
<td rowspan="2"></td><td colspan="2">Formula 44</td><td colspan="3">Model 68</td>
<td> 1/16</td><td> 1/4</td><td> 1/32</td><td> 1/16</td><td> 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td>
<td>Bloody fingerstick</td><td> 0</td><td>5G</td><td> 0</td><td>4G</td><td>7G</td>
<td>Single sided weed</td><td>10C</td><td>10C</td><td>IOC</td><td>ikoc</td><td>10C</td>
<td>Sorghum</td><td>IOC</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Deaf oats</td><td> 0</td><td>5G</td><td>8G, 7C</td><td>8G, 8C</td><td>IOC ~</td>
<td>Wild Sorghum</td><td>IOC</td><td>10C</td><td>9G, 9C</td><td>IOC</td><td>~ Toc "</td>
<td>Dallis grass</td><td>5G</td><td>8G, 3C</td><td> 0</td><td> 0</td><td>6G</td>
<td>fretsaw</td><td>3G</td><td>6G</td><td>4G, 3H</td><td>5G, 5H</td><td>9G, 9C</td>
<td>Kentucky bluegrass</td><td>8G</td><td>10E</td><td>1OE</td><td>IN</td><td>(IN</td>
<td>brome</td><td>10E</td><td>10E</td><td>8G, 9C</td><td>10E</td><td>10E</td>
<td>White beet</td><td>7G</td><td>10C</td><td>Ilocano</td><td>10C</td><td>10C</td>
<td>Maize</td><td>4G</td><td>8G, 8C</td><td>8G, 8C</td><td>10C</td><td>IOC</td>
<td>Mustard</td><td>1OE</td><td>10E</td><td>IOC</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>7G</td><td>8G</td><td>7G, 2C</td><td>7G, 5H</td><td>7G, 5H</td>
<td>amaranth</td><td>10E</td><td>10E</td><td>10E</td><td>10Ε</td><td>10E</td>
<td>cyprus</td><td>6G</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
126 541
Table 3 cd
<td> 1</td><td><sup>2</sup></td><td> 3</td><td> 4</td><td> 5</td><td>1 β</td>
<td>Cotton</td><td>4G</td><td>7G</td><td>7G</td><td>8G</td><td>8G</td>
<td>Bindweed</td><td>4G</td><td>10E</td><td>5G</td><td>7G</td><td>8G</td>
<td>Cassia</td><td>5G</td><td>7G, 2C</td><td>7G</td><td>8G, 3C</td><td>8G, 8C</td>
<td>mallow</td><td>Q</td><td>8G, 5C</td><td>7G</td><td>7G</td><td>night</td>
<td>Avicenna's lockup</td><td>5G</td><td>7G</td><td>8G, 7C</td><td>1 ° C</td><td>10C</td>
<td>Datura stramonium</td><td>2G</td><td>6G</td><td>7G</td><td>7G</td><td>8G, 5C</td>
<td>Soy</td><td>7G, 7H</td><td>8G, 8H</td><td>8G, 3H</td><td>7G, 5H</td><td>9G, 9C</td>
<td>Rice</td><td>10E</td><td>10E</td><td>10E</td><td>10 (E</td><td>10E</td>
<td>Wheat</td><td>2G</td><td>8G, 5C</td><td>4G, 2C</td><td>6G, 4C</td><td>7G, 4C</td>
Table 3 cd
<td rowspan="2"></td><td colspan="3">Formula 70</td><td colspan="3">Formula 67</td>
<td> 1/32</td><td> 1/16</td><td> ,1/4</td><td> 1/32</td><td> | 1/16</td><td>li / 4</td>
<td>Bloody fingerstick</td><td> 0</td><td> 1. 0</td><td> 0</td><td> 0</td><td> 0</td><td>4G</td>
<td>Single sided weed</td><td> 0</td><td> 0</td><td> ; 0</td><td>7G, 3C</td><td>8G, 3C</td><td>10C</td>
<td>Sorghum</td><td> 0</td><td> 0</td><td><sub>s</sub> 0</td><td>6G, 3H</td><td>5G</td><td>10C</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td> 1 0</td><td> 0</td><td> 0</td><td>6G, 3C</td>
<td>Wild Sorghum</td><td> 0</td><td>and 0</td><td> 0</td><td> 0</td><td> 0</td><td>5G, 5H</td>
<td>Dallis grass</td><td> 0</td><td> 0</td><td>and 0</td><td>4G</td><td>5G</td><td>10E</td>
<td>fretsaw</td><td> 0</td><td> , 0</td><td> . 0</td><td>3H</td><td>3H</td><td>10H</td>
<td>Kentucky bluegrass</td><td> 0</td><td> 0</td><td> 0</td><td>9G</td><td>DOE</td><td>10E</td>
<td>brome</td><td> 0</td><td> , 0</td><td>6G</td><td> 0</td><td>2G</td><td>8G, 8C</td>
<td>White beet</td><td>6G, 3H</td><td>10C</td><td>7G, 5H</td><td>4G</td><td>4G</td><td>-7Ó, 7C</td>
<td>Maize</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>4G</td><td>5G, 5H</td>
<td>Mustard</td><td> 0</td><td> ' <sup>9</sup></td><td>5G</td><td>9G</td><td>9G, 5C</td><td>10C</td>
<td>cocklebur</td><td> 0</td><td> 0</td><td> (0</td><td>3H</td><td>2H</td><td>5G, 5H</td>
<td>amaranth</td><td> 0</td><td>J <sup>0</sup></td><td>5G</td><td>IjOE</td><td>10E</td><td>10E</td>
<td>cyprus</td><td> 0</td><td> . 0</td><td>5G</td><td>5G</td><td>5G</td><td>8G</td>
<td>Cotton</td><td> 0</td><td> '0</td><td> 0</td><td> > 0</td><td> 0</td><td>3G, 3H</td>
<td>Bindweed</td><td> 0</td><td> ! 0</td><td> 0</td><td>3G</td><td>6G</td><td>4G</td>
<td>Cassia</td><td> 0</td><td>θ</td><td> 0</td><td> 0</td><td> 0</td><td>3G</td>
<td>mallow</td><td> 0</td><td> 0</td><td> 0</td><td> —</td><td> —</td><td>5G, 5H</td>
<td>Avicenna's lockup</td><td> 0</td><td><sup>1</sup> θ</td><td> 0</td><td>7G, 7C</td><td>1 ° C</td><td>10C,</td>
<td>Datura stramonium</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>2G</td><td>4G</td>
<td>Soy</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td>6G, 6H</td>
<td>Rice</td><td> 0</td><td> 0</td><td>6G, 5C</td><td>9G, 9C</td><td>7G, 5C</td><td>10E</td>
<td>Wheat</td><td> 0</td><td>; about</td><td> 0</td><td>3G</td><td>4G</td><td>6G</td>
Table 3 cd
<td rowspan="2"> '</td><td colspan="3">Chip 63</td><td colspan="3">Formula 64</td>
<td>ili / 32</td><td> 1/16</td><td> 1/4</td><td> 1/32</td><td> 1/16</td><td> 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>Bloody fingerstick</td><td> 0</td><td> 0</td><td>6G</td><td> 0</td><td>2G</td><td>7G</td>
<td>Single sided weed</td><td>iioc</td><td>10C</td><td>night</td><td>ljOC</td><td>10C</td><td>1 »E</td>
<td>Sorghum</td><td>9G, 9C</td><td>1 ° C</td><td>Ilocano</td><td>10C</td><td>| 1 (OE</td><td>1OE</td>
<td>Deaf oats</td><td>2G</td><td>6G</td><td>7G, 5C</td><td>4G</td><td>7G, 3C</td><td>10C</td>
<td>Wild Sorghum</td><td>8H, 8C</td><td>10C</td><td>10C</td><td>10C</td><td>(10C</td><td>10C</td>
<td>Dallis grass</td><td> 0</td><td>and 0</td><td>5G, 3H</td><td>5G</td><td>7G</td><td>10C</td>
<td>fretsaw</td><td>3H</td><td>4G, 3H</td><td>10C</td><td>6G, 3H</td><td>9G, 9C</td><td>10C</td>
<td>Kentucky bluegrass</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10E</td><td>10 (E</td>
<td>brome</td><td>5G</td><td>8G, 8C</td><td>1J0E</td><td>10E</td><td>IjOE</td><td>10E</td>
<td>White beet</td><td>ljOC</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
126 541
Table 3 cd
<td> 1</td><td> 2</td><td> 3</td><td> 1 <sup>4</sup> - 1</td><td><sup>5</sup></td><td> 6</td><td><sup>7</sup></td>
<td>Maize</td><td>6G, 3H</td><td>7G, 7H</td><td>10C</td><td>1 ° C</td><td>10C</td><td>10C</td>
<td>Mustard</td><td>10C</td><td>ICC</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>7G, 5H</td><td>8G, 5H</td><td>8G, 5H</td><td>8G, 5H</td><td>8G, 5H</td><td>8G, 8H</td>
<td>amaranth</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>Illo</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td><td>Λ0Ε</td><td>1ΌΕ</td>
<td>Cotton</td><td>6G</td><td>7G</td><td>9G</td><td>6G, 3H</td><td>8G, 6G</td><td>8G, 6C</td>
<td>Bindweed</td><td>8G</td><td>8G</td><td>1 ° C</td><td>9G</td><td>9G</td><td>10C</td>
<td>Cassia</td><td>8G</td><td>8G, 5H</td><td>ICC</td><td>8G, 8C</td><td>8G, 5C</td><td>8G, 9C</td>
<td>mallow</td><td> 0</td><td>6C, 5C</td><td><1 ° C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>BLANKET</td><td>10C</td><td>10C</td><td>10C</td>
<td>Datura stramonium</td><td>8G, 3C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 7C</td><td>8G, 8C</td>
<td>Soy</td><td>7G, 5H</td><td>7G, 5H</td><td>9G, 5H</td><td>8G, 5H</td><td>9G, 5H</td><td>9G, 5H</td>
<td>Rice</td><td>8G, 8C</td><td>10C</td><td>10E</td><td>8G, 9C</td><td>10C</td><td>10E</td>
<td>Wheat</td><td>2G</td><td>4G</td><td>6G,</td><td>6G</td><td>6G, 5C</td><td>10C</td>
Table 3 cd
<td rowspan="2"></td><td colspan="3">~ Pattern 65</td><td colspan="2">Formula 60</td>
<td> 1/32</td><td> | 1/16</td><td> 1/4</td><td> 1/16</td><td> 1 1/4</td>
<td>Bloody fingerstick</td><td> 0</td><td>4G</td><td>8G</td><td>3H</td><td>6G</td>
<td>Single sided weed</td><td> 0</td><td>6G, 3H</td><td>8C, 5H</td><td>6G, 4C</td><td>IOG</td>
<td>Sorghum</td><td>6G, 3H</td><td>7G, 3H</td><td>1GC</td><td>10C</td><td>10C</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td>5G, 3C</td><td>6G</td><td>8G, 5C</td>
<td>Wild Sorghum</td><td>2H</td><td>2H</td><td>6G, 5H</td><td>6G, 3H</td><td>8G, 8C</td>
<td>Dallis grass</td><td> 0</td><td> 0</td><td>4G</td><td> 0</td><td>4G</td>
<td>fretsaw</td><td> 0</td><td> 0</td><td>7G</td><td>3H</td><td>6G, 2C</td>
<td>Kentucky bluegrass</td><td>5G, 6C</td><td>7G, 8C</td><td>JOE</td><td>8G</td><td>-1OE</td>
<td>brome</td><td> 9</td><td>6G, 3C</td><td>7G, 8C</td><td>10E</td><td>1OE</td>
<td>White beet</td><td>10C</td><td>ICC</td><td>10C</td><td>8G, 8C</td><td>10C</td>
<td>Maize</td><td>7G, 7H</td><td>1 ° C</td><td>10C</td><td>5G, 5H</td><td>9G, 9C</td>
<td>Mustard</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>8G, 8H</td><td>8G, 8H</td><td>8G, 8H</td><td>8G, 5H</td><td>8G, 3H</td>
<td>amaranth</td><td>10E</td><td>10e</td><td>10E</td><td>, 10C</td><td>10C</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>JLOE</td><td>10E</td><td>10E</td>
<td>Cotton</td><td>8G</td><td>8G</td><td>10C</td><td>5G</td><td>5G ~</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>6G</td><td>8G, 8C</td>
<td>Cassia</td><td>8G, 9C</td><td>10C</td><td>10C</td><td>4G</td><td>8G, 8C</td>
<td>mallow</td><td>10C</td><td>10C</td><td>10C</td><td>6G, 5C</td><td>10C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>8G, 8C</td><td>1 ° C</td>
<td>Datura stramonium</td><td>8G, 8C</td><td>10C</td><td>8G, 9C</td><td>5G, 3H</td><td>10C</td>
<td>Soy</td><td>9G, 5H</td><td>9G, 5H</td><td>9G, 5H</td><td>8G, 8C</td><td>8G, 8C</td>
<td>Rice</td><td>5G, 3C</td><td>5G, 3C</td><td>7G, 4C</td><td>10E</td><td>IN</td>
<td>Wheat</td><td> 0</td><td> 0</td><td>2G</td><td> 0</td><td>3G</td>
Table 3 cd
<td></td><td colspan="2">Formula 61</td><td colspan="2">model 52</td>
<td></td><td> 1/16</td><td> 1/4</td><td> 1/16</td><td> ‘ 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> . 4</td><td> 5</td>
<td>Bloody fingerstick</td><td> 0</td><td>6G</td><td>6G</td><td>7G</td>
<td>Single sided weed</td><td>6G, 3H</td><td>10C</td><td>8G, 4C</td><td>8G, 6H</td>
<td>Sorghum</td><td>10C</td><td>10C</td><td>9G, 8C</td><td>10C</td>
<td>Deaf oats</td><td>6G</td><td>10C</td><td>6G, 2C</td><td>8G, 5C</td>
<td>Wild Sorghum</td><td>6G, 3H</td><td>10C</td><td>8G, 2C</td><td>10C</td>
126 541 <1
Table 3 cd
<td> 1</td><td><sup>2</sup></td><td> 1 3 ’</td><td>and '4</td><td> 1 <sup>5</sup></td>
<td>Dallis grass</td><td> 0</td><td>5G</td><td>3G</td><td>5G</td>
<td>fretsaw</td><td>2H</td><td>5G, 2C</td><td>6G</td><td>8G, 4C</td>
<td>Kentucky bluegrass</td><td>9G</td><td>10E</td><td>9G</td><td>10E</td>
<td>brome</td><td>10E</td><td>10E</td><td>7G</td><td>10C</td>
<td>White beet</td><td>7G, 8C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Maize</td><td>6G, 5H</td><td>9G, 9C</td><td>9G, 9C</td><td>10C</td>
<td>Mustard</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>6G, 2C</td><td>8G, 3C</td><td>8G, 8C</td><td>8G, 8C</td>
<td>amaranth</td><td>10C</td><td>10C</td><td>10E</td><td>10E</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>7G</td><td>9G</td>
<td>Cotton</td><td>3G</td><td><sup>8G</sup></td><td>9G, 5H</td><td>9G, 5H</td>
<td>Bindweed</td><td>4G</td><td>10G</td><td>9G, 9G</td><td>9G, 9C</td>
<td>Kas me</td><td>3G</td><td>6G</td><td>8G, 9C</td><td>10C</td>
<td>mallow</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Avioenny's lockup.</td><td>8G</td><td>10C</td><td>1 ° C</td><td>10C</td>
<td>Datura stramonium</td><td>8G, 8G</td><td>10C</td><td>5G</td><td>8G, 7C</td>
<td><sup>;</sup> Soy</td><td>7G, 5H</td><td>9G, 9C</td><td>9G, 9C</td><td>9G, 9C</td>
<td>Rice</td><td>8G, 8C</td><td>10E</td><td>6G, 3C</td><td>8G, 8C</td>
<td>Wheat</td><td>3G</td><td>5G, 2C</td><td>about |</td><td> 0</td>
Table 3 cd
<td rowspan="2"></td><td colspan="2">Formula 47</td><td colspan="2">Formula 48</td>
<td> 1/18</td><td> 1/4</td><td> 1/18</td><td> 1/4</td>
<td>Bloody fingerstick</td><td> 0</td><td>6G</td><td> 0</td><td>4G</td>
<td>Single sided weed</td><td>10C.</td><td>10C</td><td>10C</td><td>10C</td>
<td>Sorghum</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Deaf oats</td><td>8G, 3C</td><td>8G, 3C</td><td>8G, 2C</td><td>8G, 6C</td>
<td>Wild Sorghum</td><td>9G, 3C</td><td>10C</td><td>9G, 9C</td><td>1 ° C</td>
<td>Dallis grass</td><td>4G</td><td>8G, 5C</td><td>5G</td><td>8G, 9C</td>
<td>fretsaw</td><td>10C</td><td>10C</td><td>6G, 4H</td><td>1 ° C</td>
<td>Kentucky bluegrass</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>brome</td><td>10C</td><td>10E</td><td>10E</td><td>10E</td>
<td>White beet</td><td>9G, 9C</td><td>9G, 9C</td><td>9G, 9C</td><td>9G, 9C</td>
<td>Maize</td><td>5G, 3H</td><td>7G, 7H</td><td>9G, 9C</td><td>9G, 9C</td>
<td>Mustard</td><td>10C</td><td>10C</td><td>10C</td><td>1 ° C</td>
<td>cocklebur</td><td>7G, 5H</td><td>8G, 5C</td><td>8G, 5H</td><td>7G, 5H</td>
<td>amaranth</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>cyprus</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>Cotton</td><td>3G</td><td>8G</td><td>6G, 2H</td><td>8G, 5H</td>
<td>Bindweed</td><td>5G</td><td>Ilocano</td><td>10C</td><td>8G, 5C</td>
<td>Cassia</td><td>7G, 5C</td><td>8G, 7C</td><td>7G, 3C</td><td>8G, 7C</td>
<td>Slazowiiec</td><td>3H</td><td>7G, 5H</td><td>9G, 9C</td><td>10C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Datura</td><td>5G</td><td>7G</td><td>6G</td><td>8G, 7C</td>
<td>Soy</td><td>8G, 8H</td><td>9G, 9H</td><td>8G, 8H</td><td>8G, 9Ή</td>
<td>Rice</td><td>1GC</td><td>10E</td><td>10E</td><td>10E</td>
<td>Wheat</td><td>5G</td><td>6G</td><td>7G</td><td>10C</td>
<td rowspan="2"></td><td colspan="2">Formula 49</td><td colspan="2">Formula 53</td>
<td> 1/18</td><td> 1/4</td><td> 1/18</td><td> 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td>
<td>Bloody fingerstick j</td><td> 0</td><td> 0</td><td> 0</td><td>5G</td>
<td>Single sided weed</td><td>4G</td><td>4G</td><td> 0</td><td>7G, 4C</td>
126 641
Table 3 cd
<td> 1</td><td> 2</td><td> 1 3</td><td> 1 <sup>4</sup></td><td> 1 <sup>5</sup></td>
<td>Sorghum</td><td>5G</td><td>7G</td><td>8G</td><td>IOC</td>
<td>Deaf oats</td><td>3G</td><td> ;0</td><td>3G</td><td>6G</td>
<td>Wild Sorghum</td><td> 0</td><td>6G, 6E</td><td> 0</td><td>0G</td>
<td>Dallis grass</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td>
<td>fretsaw</td><td> 0</td><td>3H</td><td> 0</td><td>6G</td>
<td>Kentucky bluegrass</td><td>6G</td><td>8G</td><td>8G</td><td>1GE</td>
<td>brome</td><td> 0</td><td>3G</td><td>3G</td><td>6G</td>
<td>White beet</td><td>10C</td><td>IOC</td><td>9G, 9C</td><td>10C</td>
<td>Maize</td><td>4G, 2H</td><td>7G, 5H</td><td>5G, 3H</td><td>7G, 8H</td>
<td>Mustard</td><td>9G</td><td>IOC</td><td>10C</td><td>ioc</td>
<td>cocklebur</td><td>8G, 5H</td><td>8G, 5C</td><td>8G, 5H</td><td>8G, 8C</td>
<td>amaranth</td><td>10E</td><td>Ί0Ε</td><td>10E</td><td>10E</td>
<td>cyprus</td><td>8G</td><td>8G</td><td>7G</td><td>7G</td>
<td>Cotton</td><td>7G, 5H</td><td>8G, 5H</td><td>7G</td><td>8G</td>
<td>Bindweed</td><td>8G</td><td>8G, 5C</td><td>8G</td><td>8G, 5C</td>
<td>Cassia</td><td>7G, 3C</td><td>8G, 9C</td><td>7G, 3C</td><td>8G, 9C</td>
<td>mallow</td><td>5G, 6H</td><td>IOC</td><td>5G, 5H</td><td>ioc</td>
<td>Avdcenna Zaźle</td><td>7G, 7C</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Datura stramonium</td><td>3G</td><td>5G</td><td>3G</td><td>5G</td>
<td>Soy</td><td>3G</td><td>6G, 5H</td><td>2G, 2H</td><td>7G, 7H</td>
<td>Rice</td><td>6G, 3C</td><td>5G, 3C</td><td>6G, 3C</td><td>6G, 3C</td>
<td>Wheat</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td>
Test C. Soybeans were sown in pots filled with dust-sandy Fallsington soil. <sup>35 </sup>wool, corn, rice, wheat, sorghum, lucerne, Avicenna (Abutilon theophrasti), (Sesbania exaltata), cassia (Cassia tora), morning glory (Ipomoea spp.), datura (Datura stramonium), turnip (Xanthium pennsylvanicum) fingerstick (Digitar <sup>40 </sup>spp.), cyprus (Cyperus rotunda), unilateral weed (Echinochloa erusgalli), trichinosis (Sataria faberia) and deaf oats (Aveha fatua).
After about 2 1/2 weeks, the young plants and the soil around them were sprayed with the test compounds of formula 1 listed in Table 4, dissolved in non-toxic solvents for plants. Other groups of the same weeds and crops were treated with solvents alone for comparative testing. Fourteen days after treatment, the results of the trials were visually evaluated by comparing the plants treated with test compounds to the control plants. The results given in Table 4 indicate that many of the compounds tested do not harm wheat.
Table 4
<td rowspan="3">Tested plant</td><td colspan="5">Test compound and its quantity kg / ha</td>
<td colspan="2">Formula 39</td><td colspan="3">Formula 39</td>
<td> 1/18</td><td> 11/4</td><td> 1/500</td><td> 1/250</td><td> 1/128</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td>
<td>Soy</td><td>1GG 8C</td><td>10G 7C</td><td>10G, 8C</td><td>10G, 9C</td><td>, 10G, 9C</td>
<td>Avicenna's lockup</td><td>IOC</td><td>IOC</td><td>IOC</td><td>10C</td><td>IOC</td>
<td>Sezbania</td><td>1GG 9C</td><td>IOC</td><td>8G, 7C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>Cassia</td><td>10G 6C</td><td>10G 7C</td><td>8G, 3C</td><td>10G, 8C</td><td>10G, 6C</td>
<td>Cotton</td><td>10G 7C</td><td>10G 6C</td><td>10G, 7C</td><td>IOC</td><td>10G, 9C</td>
<td>Bindweed</td><td>10G 7C</td><td>IOC</td><td>2G</td><td>0G</td><td>7G, 3C</td>
<td>Lucerne</td><td></td><td></td><td>5G</td><td>10G, 6C</td><td>10G, 5C</td>
<td>Datura stramonium</td><td>1GG 9C</td><td>10G 9C</td><td>3G</td><td>8G, 3C</td><td>10C</td>
<td>cocklebur</td><td>10G 8C</td><td>10G 8C</td><td>10G</td><td>8G, 2C</td><td>10G, 8C</td>
<td>Maize</td><td>1GG 9C</td><td>IOC</td><td>10G, 7C</td><td>8G, 3U</td><td>10G, 9C</td>
<td>crabgrass</td><td>10G 4C</td><td>10G 8C</td><td>5G</td><td>5G</td><td>6G</td>
126 541
Table 4 cd
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 1 <sup>6</sup></td>
<td>Rice</td><td>10G 4C</td><td>10G 6C</td><td>10G, 4C</td><td>8G, 2C</td><td>10G, 5C</td>
<td>cyprus</td><td>10G 6C</td><td>10G 7C</td><td>1OG, 3C</td><td>10G, 4C</td><td>1 ° C</td>
<td>Single sided weed</td><td>10G 8C</td><td>10G 9C</td><td>10C</td><td>10G, 3C</td><td>1OG, 8C</td>
<td>Wheat</td><td>10G 7C</td><td>1OG 7C</td><td>1OG, 9C</td><td>8G</td><td>1OG, 4C</td>
<td>fretsaw</td><td>10G 7C</td><td>10G 8C</td><td>10G, 8C</td><td>8G</td><td>10G, 7C</td>
<td>Deaf oats</td><td>10G 8C</td><td>10G 9C</td><td>8G, 3C</td><td>8G</td><td>1OG, 5C</td>
<td>Sorghum</td><td>10G 9C</td><td>10G 8C</td><td>10G, 3C</td><td>10G, 4C</td><td>1OG, 7C</td>
Table 4 cd
<td rowspan="2"></td><td colspan="2">Formula 39</td><td colspan="3">Formula 40</td>
<td>1/64 -ABOUT-</td><td> 1732</td><td> 1/64</td><td> 1/32</td><td> 1/16</td>
<td>Soy</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td><td>10G, 9C</td><td>R) G, 8C</td>
<td>Avicenna's lockup</td><td>10G, 8C</td><td>10C</td><td>10C</td><td>10C</td><td> —</td>
<td>Sezbania</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td>
<td>Cassia</td><td>10G, 8C</td><td>1OG, 8C</td><td>10G, 9C</td><td>ilOG, 8C</td><td>10G, 9C</td>
<td>Cotton</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 7C</td>
<td>Bindweed</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>, 10C</td><td>10C</td>
<td>Lucerne</td><td>10G, 8C</td><td>10G, 8C</td><td>(1OG, 9C</td><td>10C</td><td>10C, 9C</td>
<td>Datura stramonium</td><td>10G, 9C</td><td>10C</td><td>1 ° C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>10G, 7C</td><td>10C</td><td>10G, 9C</td><td>10G, 9C</td><td>10C</td>
<td>Maize</td><td>10G, 9C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 7C</td><td>10G, 9C</td>
<td>crabgrass</td><td>6G</td><td>1OG, 4C</td><td>3G</td><td>7G, 3C</td><td>10G, 5C</td>
<td>Rice</td><td>10G, 6C</td><td>10G, 6C</td><td>10G, 3C</td><td>10G, 4C</td><td>10G, 6C</td>
<td>cyprus</td><td>10G, 8C</td><td>10G, 9C</td><td>10G, 6C</td><td>10G, 6C</td><td>10G, 8C</td>
<td>Single sided weed</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 7C</td><td>10G, 9C</td>
<td>Wheat</td><td>10G, 9C</td><td>1OG, 7C</td><td>10G, 8C</td><td>10G, 7C</td><td>10G, 9C</td>
<td>fretsaw</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 7C</td><td>10G, 7C</td><td>10C</td>
<td>Deaf oats</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 9C</td><td>, 10G, 8C</td>
<td>Sorghum</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 9C</td>
Table 4 CDs
<td rowspan="2"></td><td colspan="3">Formula 41</td><td colspan="3">Formula 42</td>
<td> 1/64</td><td> ,1/32</td><td> | 1/16</td><td> (1/64</td><td> 1/32</td><td> | 1/16</td>
<td>Soy</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td> —</td><td>10C</td><td>10C</td>
<td>Sezbania</td><td>10G, 9C</td><td>10G, 9C</td><td>ilOG, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>liOG, 9C</td>
<td>Cassia</td><td>10G, 8C</td><td>1 ° C</td><td>10G, 9C</td><td>10G, 7C</td><td>10G, 9C</td><td>10G, 8C</td>
<td>Cotton</td><td>10G, 6C</td><td>1ÓG, 6C</td><td>10G, 8C</td><td>10G, 5C</td><td>10G, 8C</td><td>10G, 8C</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10G, 9C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Lucerne</td><td>10G, 9C</td><td></td><td>10G, 9C</td><td>10G, 8C</td><td>10G, 9C</td><td>10G, 9C</td>
<td>Datura stramonium</td><td>10C</td><td>Loc</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>/ 10C</td><td>10G, 8C</td><td>10C</td><td>10C</td>
<td>Maize</td><td>10G, 7C</td><td>10G, 8C</td><td>10G, 8C</td><td>9G, 3C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>crabgrass</td><td>. 4G</td><td>5G, 2C</td><td>3H, 2C</td><td> 0</td><td>3G, 2H</td><td>5G, 2C</td>
<td>Rice</td><td>1OG, 4C</td><td>1OG, 4C</td><td>1, OG, 4C</td><td>7G</td><td>10G, 2C</td><td>10G, 4C</td>
<td>cyprus</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td> 0</td><td>4G</td><td>2G</td>
<td>Single sided weed</td><td>10G, 7C</td><td>10G, 9C</td><td>10G, 8C</td><td>8G, 5H</td><td>10G, 6C</td><td>10G, 7C</td>
<td>Wheat</td><td>8G, 3C</td><td>, 10G, 7C</td><td>10G, 8C</td><td>7G, 3H</td><td>5G</td><td>5G</td>
<td>fretsaw</td><td>1HOR, 9C</td><td>10G, 9C</td><td>10C</td><td>10G, 2C</td><td>10G, 7C</td><td>10G, 4C</td>
<td>Deaf oats</td><td>10G, 6C</td><td>10G, 5C</td><td>8G, 4C</td><td>6G</td><td>10G, 2C</td><td>10G, 3C</td>
<td>Sorghum</td><td>10G, 8C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 2C</td><td>10G, 5C</td><td>10G, 5C</td>
126 541
Table 4 cd
<td rowspan="2"></td><td colspan="3">Formula 43</td><td colspan="2">Formula 44</td>
<td> 1/64</td><td> 1/32 ·.</td><td> | 1/16</td><td> 1/16</td><td> 1/4</td>
<td>Soy</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>Avicenna's lockup</td><td> —</td><td> —</td><td>IOC</td><td>5G</td><td>IOC</td>
<td>Sezbania</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>IOC</td><td>IOC</td>
<td>Cassia</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td><td>1OG, 8C</td>
<td>Cotton :</td><td>10G, 5> C</td><td>10G, 9C</td><td>10G, 8C</td><td>5G, 2C</td><td>7G> 3H</td>
<td>Bindweed</td><td>10G, 9C</td><td>IOC</td><td>Ilocano</td><td>4G</td><td>9G, 3C</td>
<td>Lucerne</td><td> —</td><td>8G, 6C</td><td>10G, 6C</td><td>2C</td><td>1OG, 6C</td>
<td>Datura stramonium</td><td>10G, 9C</td><td>IOC</td><td>IOC</td><td>4G, 2C</td><td>6G, 2C</td>
<td>cocklebur</td><td>10G, 2C</td><td>10G, 7C</td><td>10G, 9C</td><td>3G, 3C</td><td>9G, 6C</td>
<td>Maize</td><td>8G, 4H</td><td>8G, 2C</td><td>9G, 4C</td><td>6G, 3H</td><td>10G, 7C</td>
<td>crabgrass</td><td> 0</td><td> 0</td><td>2G</td><td> 0</td><td>2G</td>
<td>Rice</td><td>6G</td><td>10G, 2C</td><td>10G, 3C</td><td>10G, 8C</td><td>1OG, 7C</td>
<td>cyprus</td><td> 0</td><td> 0</td><td>5G, 2C</td><td>10G, 3C</td><td>10G, 3C</td>
<td>Single sided weed</td><td>6G, 2ΙΪ;</td><td>9G, 3H</td><td>10G, 5H</td><td>10G, 4C</td><td>1H, 5C</td>
<td>Wheat</td><td>3G, 2H</td><td>3G</td><td>3G</td><td>8G</td><td>1OG</td>
<td>fretsaw</td><td>3G</td><td>7G</td><td>10G, 3C</td><td>5G</td><td>8G</td>
<td>Deaf oats</td><td> 0</td><td>2G</td><td>3G, 2C</td><td>5G</td><td>8G</td>
<td>Sorghum</td><td>5G, 2H</td><td>10G, 4H</td><td>10G, 4H</td><td>10G, 6C</td><td>LOG, 6C</td>
Table 4 cd
<td></td><td></td><td>Formula 70</td><td></td><td></td><td>Formula 63</td><td></td>
<td></td><td> 1/32</td><td> 1 1/16</td><td> 1/4</td><td> 1/32</td><td> 1/16</td><td> 1/4 ·</td>
<td>Soy</td><td> 0</td><td> 0</td><td>5G, 2G</td><td>10G, 8C</td><td>10G, 8C</td><td>IOC</td>
<td>Avicenna's lockup</td><td> 0</td><td> 0</td><td>5G</td><td>10C</td><td>IOC</td><td>IOC</td>
<td>Sezbania</td><td> 0</td><td>3G</td><td>7G</td><td>10G, 9C</td><td>IOC</td><td>IOC</td>
<td>Cassia</td><td> 0</td><td> 0</td><td>5G, 3C</td><td>10G, 8C</td><td>10G, 8C</td><td>1OG, 9C</td>
<td>Cotton</td><td> 0</td><td> 0</td><td>5G</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Bindweed</td><td> 0</td><td> 0</td><td>5G</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Lucerne</td><td> 0</td><td> 0</td><td>3G</td><td>IOC</td><td>MC</td><td>IOC</td>
<td>Datura stramonium</td><td> 0</td><td> 0</td><td>2G</td><td>IOC</td><td>MC</td><td>IOC</td>
<td>cocklebur</td><td> 0</td><td> 0</td><td>3G</td><td>IOC</td><td>Ilocano</td><td>IOC</td>
<td>Maize</td><td> 0</td><td> 0</td><td>8G, 5H</td><td>8G, 3H</td><td>10G, 3C</td><td>10G, 8C</td>
<td>crabgrass</td><td> 0</td><td> 0</td><td> 0</td><td>5G</td><td>5G</td><td>9G, 3C</td>
<td>Rice</td><td> 0</td><td>3G</td><td>8G</td><td>10G, 6C</td><td>10G, 5C</td><td>10G, 6C</td>
<td>cyprus</td><td> 0</td><td>3G</td><td>8G</td><td>10G, 8C</td><td>10G, 9C</td><td>ilOG, 8C</td>
<td>Single sided weed</td><td> 0</td><td> 0</td><td>4G</td><td>10G, 8C</td><td>10G, 9C</td><td>10G, 9C</td>
<td>Wheat</td><td> 0</td><td> 0</td><td>4G</td><td>8G</td><td>10G</td><td>10G, 3H</td>
<td>fretsaw</td><td> 0</td><td> 0</td><td>2G</td><td>10G</td><td>10G</td><td>10G, 3C</td>
<td>Deaf oats</td><td> 0</td><td> 0</td><td>3G</td><td>10G</td><td>10G</td><td>10G, 3C</td>
<td>Sorghum</td><td> 0</td><td>4G</td><td>8G, 3H</td><td>10G, 5C</td><td>IOC</td><td>10G, 8C</td>
Table 4 cd
<td></td><td></td><td>Formula 64</td><td></td><td></td><td>Formula 65</td><td></td>
<td></td><td> 1/32</td><td> 1/16</td><td><sup>1/4</sup></td><td> 1/32</td><td> 1/16</td><td> 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td>
<td>Soy</td><td>10G, 8C</td><td>1OG, 8C</td><td>10G, 8C</td><td>1OG, 8C</td><td>10G.9C</td><td>1OG, 8C</td>
<td>Avflfcense Blame</td><td>IOC</td><td>ioc</td><td> —</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Sezbania</td><td>10G, 9C</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Cassia</td><td>1OG, 8C</td><td>10G, 8C</td><td>1OG, 8C</td><td>1OG, 9C</td><td>10G, 9C</td><td>1OG, 9C</td>
<td>Cotton</td><td>IOC</td><td>IOC</td><td>IOC</td><td>1OG, 7C</td><td>IOC [</td><td>IOC</td>
126 541
Table 4 cd
<td> 1</td><td><sup>2</sup> 1</td><td> 3 |</td><td> 4 |</td><td> 5</td><td> 6 |</td><td> 7</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Lucerne</td><td>10C</td><td>10C</td><td>10C</td><td>10G, 9C</td><td>10C</td><td>1 ° C</td>
<td>Datura stramonium</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C '</td><td>10C</td>
<td>cocklebur</td><td>10G, 9C</td><td>10C</td><td>10C</td><td>10C</td><td> —</td><td>10C</td>
<td>Maize</td><td>8G, 3C</td><td>7G, 3C</td><td>10G, 9C</td><td> —</td><td>8G, 5H</td><td>10G, 4C</td>
<td>crabgrass</td><td>8G</td><td>8G</td><td>10G, 3C</td><td> 0</td><td>3G</td><td>7G</td>
<td>Rice</td><td>10G, 5C</td><td>10G, 4C</td><td>10G, 6C</td><td>6G</td><td>8G</td><td>10G, 4C</td>
<td>cyprus</td><td>10G, 8C</td><td> ~ 80730<sup>-</sup></td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td><td>10C</td>
<td>Single sided weed</td><td>10G, 8C</td><td>10G, 6C</td><td>10G, 8C</td><td>7G, 3H</td><td>8G, 3H</td><td>8G, 3H</td>
<td>Wheat</td><td>9G</td><td>10G, 3C</td><td>10G, 5C</td><td> 0</td><td> 0</td><td> 0</td>
<td>fretsaw</td><td>10G</td><td>10G</td><td>10G, 6C</td><td>2G</td><td> 0</td><td>5G</td>
<td>Deaf oats</td><td>10G</td><td>10G, 3C</td><td>10G, 5C</td><td>5G</td><td>5G</td><td>8G</td>
<td>Sorghum</td><td>10G, 4C</td><td>ί ΐοάζ 3C</td><td><sub>t</sub>10G, 8C</td><td>8G, 3H</td><td>10G, 3H</td><td>10G, 3H</td>
Table 4 cd
<td rowspan="2"></td><td colspan="3">Wizor 68</td><td colspan="3">Formula 67</td>
<td> 1/32</td><td> 1/16</td><td> | 1/4</td><td> 1/32</td><td> ( 1/16</td><td> 1/4</td>
<td>Soy</td><td>10G, 8C</td><td>10C</td><td>10G, 9C</td><td>10G, 3C</td><td>10G, 6C</td><td>10C, 6C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>10G, 7C</td><td>10C</td><td>10C</td>
<td>Sezbania</td><td>10C</td><td>10C</td><td>10G, 9C</td><td>10G, 5C</td><td>10G, 7G</td><td>10G "8C</td>
<td>Cassia</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>3G</td><td>4G</td><td>8G, 3C</td>
<td>Cotton</td><td>10G, 9C</td><td>10C</td><td>10C</td><td>10G, 4C</td><td> —</td><td>10G, 8C</td>
<td>Bindweed</td><td>10C</td><td>1 ° C</td><td>10C</td><td>10G, 3B</td><td>10G, 5B</td><td>10B</td>
<td>Lucerne</td><td>10C</td><td>10C</td><td>10C</td><td>10G, 6C</td><td>10C, 6C</td><td>10C, 9C</td>
<td>Datura stramonium</td><td>10G, 9C</td><td>10C</td><td>10C</td><td>8G, 3C</td><td>8G, 3C</td><td>10G, 6C</td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>night</td><td>10G, 4C</td><td>ϊόά, κΓ</td><td>10C, 6C</td>
<td>Maize</td><td>10G, 9C</td><td>10G, 9C</td><td>10C</td><td>5G, 2H</td><td>8G, 3H</td><td>10G, 3H</td>
<td>crabgrass</td><td>5G</td><td>7G</td><td>10G, 3C</td><td> 0</td><td> 0</td><td>about</td>
<td>Rice</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 7C</td><td>8G</td><td>10G, 2C</td><td>10G, 4C</td>
<td>cyprus</td><td>10C</td><td>10C</td><td>10C</td><td>3G</td><td>8G</td><td>9G</td>
<td>Single sided weed</td><td>10G, 8C</td><td>10G, 7C</td><td>10G, 9C</td><td>8G, 2G</td><td>10G, 3C</td><td>10G, 3C</td>
<td>Wheat</td><td>8G</td><td>10G, 3C</td><td>10G, 4C</td><td> 0</td><td>3G</td><td>5G</td>
<td>fretsaw</td><td>7G</td><td>10G</td><td>10G, 3C</td><td>7G</td><td>7G</td><td>10G, 3H</td>
<td>Deaf oats</td><td>10G, 6C</td><td>10G, 5C</td><td>10G, 7C</td><td>6G</td><td>7C</td><td>9G</td>
<td>Sorghum</td><td>10C</td><td>KOG, 8C</td><td>1 | OC</td><td>5G</td><td>10G, 3H</td><td>10G, 3H</td>
Table 4 cd
<td rowspan="2"></td><td colspan="2">Formula 49</td><td colspan="2">Formula 53</td>
<td> 1/16</td><td> 1/4</td><td> 1/16</td><td> 1/4</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td>
<td>Soy</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>LOG, 9C</td>
<td>Avicenna's lockup</td><td> —</td><td>10C</td><td>10C</td><td> —</td>
<td>Sezbania</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Cassia</td><td>10G, 9C</td><td>10C</td><td>10G, 9C</td><td>10C</td>
<td>Cotton</td><td>10G, 9C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Lucerne</td><td>5G</td><td>10G, 9C</td><td>10C</td><td>10C</td>
<td>Datura stramonium</td><td>8G, 4C</td><td>10G, 4C</td><td>10G, 5C</td><td>10G, 8C</td>
<td>cocklebur</td><td>10C</td><td> —</td><td>10C</td><td>10C</td>
<td>Maize</td><td>5G</td><td>8G, 2C</td><td>10G, 3H</td><td>10G, 3C</td>
<td>crabgrass</td><td>3G</td><td>4G</td><td> 0</td><td>3G</td>
126 541
Table 4 cd
<td> 1</td><td> 2</td><td>1 a </td><td>and 4</td><td> 1 5</td>
<td>Rice</td><td>4G</td><td>6G</td><td>4G</td><td>7G</td>
<td>cyprus</td><td>10G, 4C</td><td>10G, 4C</td><td>5G</td><td>9G, 4C</td>
<td>Single sided weed</td><td>7G</td><td>8G</td><td>6G</td><td>8G</td>
<td>Wheat</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td>
<td>fretsaw</td><td> 0</td><td> 0</td><td> 0</td><td>3G</td>
<td>Deaf oats</td><td> 0</td><td>5G</td><td>3G</td><td>5G</td>
<td>Sorghum</td><td>6G j</td><td>8G</td><td>10G, 3H</td><td>10G</td>
Table 4 cd
<td></td><td colspan="2">Formula 52</td><td colspan="2">Formula 47</td><td colspan="2">Formula 48</td>
<td></td><td> 1/16</td><td> 1/4</td><td> 1/16</td><td> 1/4</td><td> 1/16</td><td> 1/4</td>
<td>Soy</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td><td>10G, 9C</td>
<td>Avicenna's lockup</td><td>10G</td><td> — '</td><td>10C</td><td> —</td><td> —</td><td> —</td>
<td>Sezbania</td><td>10C</td><td>10C</td><td>1OG, 9C</td><td>10C</td><td>10C</td><td>16C</td>
<td>Cassia</td><td>10C</td><td>10G, 9C</td><td>10G, 8C</td><td>10C</td><td>10C</td><td>10C</td>
<td>Cotton</td><td>10C</td><td>10C</td><td>10G, 8C</td><td>1OG, 9C</td><td>10C</td><td>10G, 8C</td>
<td>Bindweed</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10G, 9C</td><td>10G, 9C</td>
<td>Lucerne</td><td>. 10C</td><td>10C</td><td>10G, 9C</td><td>10C</td><td>ICC</td><td>10C</td>
<td>Datura</td><td>10G, 6C</td><td>10G, 7C</td><td>8G, 3C</td><td>10G, 5C</td><td>16G, 7C</td><td>1OG, 8C</td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td> —</td><td>1 ° C</td>
<td>Maize</td><td>10G, 2C</td><td>10G, 8C</td><td>8G, 2C</td><td>9G, 2C</td><td>1OG, 5C</td><td>10G, 3C</td>
<td>crabgrass</td><td>4G</td><td>7G</td><td>5G</td><td>8G, 2C</td><td>4G</td><td>7G</td>
<td>Rice</td><td>7G</td><td>10G, 2C</td><td>IIIOG, 4C</td><td>10G, 5C</td><td>10G, 4C</td><td>1OG, 5C</td>
<td>cyprus</td><td>8G, 3C</td><td>10C</td><td>10G, 6C</td><td>10G, 6C</td><td>10G, 8C</td><td>1OG, 5C</td>
<td>Single sided weed</td><td>7G</td><td>10G, 3C.</td><td>10G, 7C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 8C</td>
<td>Wheat</td><td> 0</td><td>3G</td><td>6G</td><td>1OG</td><td>10G</td><td>CbOG, 4C</td>
<td>fretsaw</td><td> 0</td><td>7G</td><td>10G, 7C</td><td>10G, 9C</td><td>, 1X) G, 3C</td><td>10G, 9C</td>
<td>Deaf oats</td><td>3G</td><td>8G</td><td>8G</td><td>10G, 3C</td><td>10G, 2C</td><td>10G, 2C</td>
<td>Sorghum</td><td>8G, 5H</td><td>8G, 2C</td><td>10G</td><td>10G</td><td>1OG</td><td>1OG, 2C</td>
Table 4 cd
<td rowspan="2"></td><td colspan="2">Formula 60</td><td colspan="2">Formula 61</td>
<td> 1/16</td><td> 1/4</td><td> 1/16</td><td> 1/4</td>
<td>Soy</td><td>10G, 7C</td><td>10G, 8C</td><td>10G, 7C</td><td>ilOG, 7C</td>
<td>Avicenna's lockup</td><td>10C</td><td>10C</td><td>10C</td><td>1 ° C</td>
<td>Sezbania</td><td>10C</td><td>10C</td><td>10G, 7C</td><td>10G, 9C</td>
<td>Cassia</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 7C</td><td>10G, 7C</td>
<td>Cotton</td><td>10G, 7C</td><td>ilOG, 9C</td><td>10G, 6C '</td><td>10G, 9C</td>
<td>Bindweed</td><td>10G, 9G</td><td>10C</td><td>10C</td><td>10C</td>
<td>Lucerne</td><td>10G, 9C</td><td>10G, 9C</td><td>1OG, 9C</td><td>10G, 9C</td>
<td>Datura</td><td>10G, 3C</td><td>1OG, 6C</td><td>10G, 8C</td><td>10G, 8C</td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>10C</td><td>10G, 9C</td>
<td>Maize</td><td>4G</td><td>7G, 3H</td><td>10G, 5H</td><td>8G</td>
<td>crabgrass</td><td> 0</td><td>4G</td><td> 0</td><td>5G</td>
<td>Rice</td><td>10G, 3C</td><td>10G, 3C</td><td>8G, 2C</td><td>10G, 6C</td>
<td>cyprus</td><td>10G, 5C</td><td>10G, 8C</td><td>7G, 2C</td><td>7G, 3C</td>
<td>Single sided weed</td><td>10G, 3H</td><td>10G, 4C</td><td>8G, 3C</td><td>10G, 6C</td>
<td>Wheat</td><td>2G</td><td>7G</td><td>4G</td><td>8G</td>
<td>fretsaw</td><td> 0</td><td>5G, 2C</td><td>2G</td><td>6G</td>
<td>Deaf oats</td><td>5G</td><td>8G, 3H</td><td>10G</td><td>8G, 3C</td>
<td>Sorghum</td><td>10G</td><td>10G, 2C</td><td>10G</td><td>10G</td>
126 541
Test D. This test demonstrates the strong herbicidal activity of one of the active compound compounds of the invention according to the invention when used before emergence. Plastic containers o<sup>5 </sup>25 cm in diameter, filled with dust-sandy Fallsington soil. In one group of containers, weeds were sown, mixing their seeds evenly with the upper layer of soil 1.2 cm thick.
The following weeds were planted in this group: grizzly sorghum (Sorghum holepense), single-sided weed (Echinochloa crusgalli), bloody burner (Digitaria sanguinalis), trichinosis (Sataria faberia), rosewood Avicenny (Abutilon theophrasti), Datura woodweed (Datura) , mustard (Brassica arvensis) and amaranth (Amaranthus retroflexus). In another group of containers, 1-4 plants useful for each container were sown, namely: corn (at a depth of 3.7 cm), cotton, sunflower, oats of the Clinton variety, wheat, beans of the Black Valentine variety, rice, sorghum, peas, flax and peanut (all 2.5 cm deep) and tomatoes, spinach, barley and panicle (all 1.2 cm deep).
Immediately after sowing, the soil surface in the containers was treated with a solution of the compound of formula 39 in a non-toxic solvent for plants, with each container group leaving one untreated container as a comparative test.
Then all containers were sprinkled with water simulating a rainfall of about 4 mm and left in the greenhouse. After 28 days, the results were evaluated similarly to those described in test A. The background results are given in Table 5.
Table 5
<td rowspan="2">Plants tested</td><td colspan="4">Test compound of formula 39 L and its quantity kg / ha</td>
<td> 1/64</td><td> | ,1/32</td><td> | 1/16</td><td> | 1/8</td>
<td>Maize</td><td> —</td><td> —</td><td> —</td><td>loc</td>
<td>Cotton</td><td> —</td><td> —</td><td> —</td><td>9G, 9C</td>
<td>Soy</td><td> —</td><td> —</td><td></td><td>9G, 9H</td>
<td>Peanut</td><td> —</td><td> —</td><td> —</td><td>10E</td>
<td>sunflower</td><td> —</td><td> —</td><td> —</td><td>8G, 7C</td>
<td>Oat</td><td> —</td><td> —</td><td> —</td><td>8G, 9C</td>
<td>Wheat</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Sorghum</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>White beet</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Pea</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Flax</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Lucerne</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Bean</td><td> —</td><td> —</td><td> —</td><td>7G, 8H</td>
<td>Spinach</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Cabbage</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Tomato</td><td> —</td><td> —</td><td></td><td>8G, 8C</td>
<td>Rice</td><td> —</td><td> —</td><td> —</td><td>10 E.</td>
<td>safflower</td><td> —</td><td> —</td><td> —</td><td>9G, OC</td>
<td>Cucumber</td><td> —</td><td> —</td><td></td><td>8G, 7G</td>
<td>Kentucky bluegrass</td><td> —</td><td> —</td><td> —</td><td>10C</td>
<td>Barley</td><td> —</td><td></td><td> —</td><td>9G, 8C</td>
<td>Tobacco</td><td> —</td><td> —</td><td> —</td><td>5G, 2C</td>
<td>Broad-leaved weeds</td><td>7G, 5C</td><td>8G, 8C</td><td>9G, 8C</td><td> —</td>
<td>Grass weeds</td><td>6G</td><td>8G, 6C</td><td>8G, 8C</td><td> —</td>
Test E. This test demonstrates the usefulness of some compounds of formula I for controlling broadleaf weeds and cyprus before and after emergence of plants in young wheat and barley crops. Containers with a diameter of 25 cm, made of plastic material, were filled with fertilized Dust-Sandy Fallsington soil sown twice, with an interval of 10 days, the following weeds: mustard (Brassica arvensts), turnip «5 (Xanthium spp.), morning glory (Ipomoea hederacea), cassia (Cassia tora), Avicenna's thistle (Abutilon theophresti), lucerne (as indicator for this species), Μ titlet (Kochia scoparia), sezbania (Sesbania exaltata), spiny brine (Salsola kali), Datura strata (Datura stramonium) and cyprus (Cyperus rotundus).
Separately, wheat and barley were sown in pots 15 cm in diameter with the same soil, simultaneously with the first weed planting. Immediately after the second weed sowing, all plants were treated with solutions of test compounds in a non-toxic solvent for plants. At that time, the wheat was about 15-15.5 cm high, barley 12.5- 15 cm and both of these plant species were in the second leaf stage, and the weeds weeded first had a height of 2> 5-12.5 cm.
the cyprus (Cyperus rotundus) were planted at a depth of about 2 m in dusty-sandy Fallsington soil in plastic pots with a diameter of 10 cm, placing 5 tubers in each pot. Solutions of compounds of formula I in a non-toxic plant solvent were treated
- land or plants at a ratio of 560 liters / ha, using 4 methods of treatment, namely spraying Table 6
<td rowspan="2">Plants tested before emergence</td><td colspan="4">Test compound of formula 65 and its quantity kg / ha</td><td colspan="4">Test compound of formula 106 and its quantity kg / ha</td>
<td> 1/256</td><td> 1/128</td><td> 1/64</td><td> 1/32</td><td> 1/256</td><td> 1/128 |</td><td> 1/64</td><td> 1/32</td>
<td>Mustard</td><td>9G, 9C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>IOC</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>7G, 7H</td><td>8G, 8H</td><td>8G, 8H</td><td>8G, 9H</td><td>8G, 8C</td><td>8G, 8H</td><td>8G, 8H</td><td>8G, 9H</td>
<td>Bindweed</td><td>8G, 7C</td><td>8G, 7C</td><td>8G, 7C</td><td>8G, 9C</td><td>8G, 6C</td><td>9G, 9C</td><td>10C</td><td>10C</td>
<td>Cassia</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 8C</td><td>8G, 5C</td><td>8G, 5C</td><td>8G, 9C</td><td>8G, 8C</td>
<td>Avicenna's lockup</td><td>8G, 3H</td><td>8G, 3H</td><td>8G, 5H</td><td>9G, 5H</td><td>9G, 8C</td><td>9G, 9C</td><td>10C</td><td>10C</td>
<td>Lucerne</td><td>5G</td><td>5G, 2C</td><td>5G</td><td>8G, 7C</td><td>7G</td><td>7G, 2C</td><td>9G, 8C</td><td>9G, 7C</td>
<td>Sesbania</td><td>7G, 3C</td><td>8G, 9C</td><td>8G, 9C</td><td>9G, 9C</td><td>7G, 3C</td><td>7G, 5C</td><td>8G, 8C</td><td>10C</td>
<td>Mietelnik</td><td>9G, 9C</td><td>IOC</td><td>10C</td><td>IOC</td><td>9G, 9C</td><td>IOC</td><td>10C</td><td>10C</td>
<td>Spiky brine</td><td>5C</td><td>7C</td><td>7C</td><td>9C</td><td>7C</td><td>8C</td><td>10C</td><td>10C</td>
<td>Datura stramonium</td><td>7G, 2C</td><td>8G, 7C</td><td>8G, 9C</td><td>8G, 9C</td><td>7G, 6C</td><td>7G, 5C</td><td>8G, 9C</td><td>8G, 7C</td>
<td>cyprus</td><td>7G</td><td>8G</td><td>9G</td><td>10E</td><td>6G, 3C</td><td>7G, 2C</td><td>8G</td><td>8G</td>
Table 6 cd
<td rowspan="2">Plants tested after emergence</td><td colspan="4">. Test compound of formula 65 and its quantity kg / ha</td><td colspan="4">Test compound of formula 106 and its quantity kg / ha</td>
<td> 1/256</td><td> 1/128</td><td> | 1/64</td><td> 1/32</td><td> 1/256</td><td>And 1/128</td><td> | 1/64</td><td> 1/32</td>
<td>Mustard</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>cocklebur</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>10C</td><td>ioc</td><td>IOC</td>
<td>Bindweed</td><td>10C</td><td>ioc<sup>-</sup></td><td>10C</td><td>10C</td><td>10C</td><td>(10C</td><td>ioc</td><td>IOC</td>
<td>Cassia</td><td>9C</td><td>FOC ~</td><td>, 10C</td><td>10C</td><td>10C</td><td>9C</td><td>Lioce</td><td>IOC</td>
<td>Avicenna's lockup</td><td> —</td><td>IOC</td><td>IOC</td><td> —</td><td> —</td><td>10C</td><td> —</td><td> —</td>
<td>Lucerne</td><td>5G</td><td>IOC</td><td>"1ÓĆ"</td><td>IOC</td><td>Ήόδ</td><td>10C</td><td>10C</td><td>IOC</td>
<td>Sezbania</td><td>night</td><td>"" 10c</td><td>10C</td><td>10C</td><td>ioc</td><td>10C</td><td>Lioce</td><td>IOC</td>
<td>Mietelnik</td><td> —</td><td> —</td><td>; 10C</td><td> —</td><td>ioc</td><td> —</td><td>IOC</td><td> —</td>
<td>Spiky brine</td><td>8C</td><td>IOC</td><td>10C</td><td>10C</td><td>ioc</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Datura stramonium</td><td>7G, 5C</td><td>Tog75C</td><td>ioa, 7C</td><td>10G, 6C</td><td>10G, 4C</td><td>10G, 8C</td><td>10G, 8C</td><td>10G, 9C</td>
<td>cyprus</td><td>7G, 3C</td><td>10G, 8C</td><td>10G, 5C</td><td>10G</td><td>3G</td><td>5G, 3C</td><td>10G, 7C</td><td>IOC</td>
<td></td><td> 1/8</td><td> 1/4</td><td colspan="2"> 1/2</td><td> 1/8</td><td> 1/4</td><td colspan="2"> 1/2</td>
<td>Wheat</td><td>2G</td><td>2G, 2C</td><td colspan="2">6G, 3C</td><td> 0</td><td> 0</td><td colspan="2">5G, 3C</td>
<td>Barley</td><td> 0</td><td>6G, 2C</td><td colspan="2">8G, 3C</td><td>5G</td><td>5G, 2C</td><td colspan="2">7G, 3C</td>
The compounds tested were used in an amount of 0.004, 0.007, 0JJL5 and 0.030 kg / ha for weeds and 0.12, 0.25 and 0.50 kg / ha for wheat and barley. The results in the post-emergence trial were evaluated after 21 days and in the pre-emergence trial after 28 days. Plant condition was assessed visually and results using the criteria described in test A are given in table 6.
Test F. This test showed that numerous compounds of formula 1 are suitable for controlling cyprus. Ground surface tubers, tuber sprinkling, soil mixing and crop treatment after emergence.
Sprinkling of the soil surface was carried out immediately after planting of the tubers, when the tubers were sprouted
The ground next to them was also sprayed and then the tubers were covered with soil. When mixed with the soil, the tubers were covered with a layer of soil treated with the test compound, and when treated after emergence, the leaves of cyprus having a height were sprayed<sup>63</sup> about 12 cm and the soil was sprayed next to ro126 541 saliva. In tests using soil surface spraying, tuber spraying and soil mixing, pots after treatment were sprayed with water, imitating 0.3 cm of water fall within 90 minutes, and then placed in a greenhouse.
In the post-emergence test, the pots were placed in a greenhouse and watered so as not to rinse off the leaves of the test medium. The results were evaluated 4 weeks after treatment. These results are given in Table 7.
T ab 1 and 7
Cyprus trial, results after 4 weeks
<td rowspan="2">Formula of the compound used and amount of compound in kg / ha</td><td colspan="4">Method of application of the test compound</td>
<td>on the surface of the earth</td><td>on tubers</td><td>mixing with the ground</td><td>after the emergence of plants</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td>
<td>Compound of formula 39</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>8E, 9G</td><td>10E</td><td>10E</td><td>4C, 7G</td>
<td> 0,008</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td> 0,016</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td> 0,032</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,064</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 40</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>8E, 9G</td><td>10E</td><td>10E</td><td>5C, 7G</td>
<td> 0,008</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td> 0,016</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td> 0,032</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,064</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 41</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>9E, 9G</td><td>8E, 9G</td><td>8E, 9G</td><td>8C</td>
<td> 0,008</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,016</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,032</td><td>10E</td><td>10E</td><td>10E</td><td>OC</td>
<td> 0,064</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 42</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>4C, 7G</td><td>5C, 8G</td><td>5C, 8G</td><td> 0</td>
<td> 0,008</td><td>4C, 7G</td><td>5C, 8G</td><td>5C, 8G</td><td>2G</td>
<td> 0,016</td><td>4C, 7G</td><td>5C, 9G</td><td>5C, 8G</td><td>2G</td>
<td> 0,032</td><td>5C, 8G</td><td>5C, 9G</td><td>5C, 9G</td><td>2C, 5G</td>
<td> 0,064</td><td>5C, 8G</td><td>5C, 9G</td><td>6C, 9G</td><td>5C, 7G</td>
<td>Compound of formula 43</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>3C, 6G</td><td>3C, 7G</td><td>3C, 7G</td><td> 0</td>
<td> 0,008</td><td>4C, 8G</td><td>4C, 8G</td><td>4C, 8G</td><td> 0</td>
<td> 0,016</td><td> —</td><td>4C, 8G</td><td>4C, 8G</td><td>2C, 3G</td>
<td> 0,032</td><td>4C, 8G</td><td>4C, 8G</td><td>4C, 8G</td><td>3G</td>
<td> 0,064</td><td>5C, 8G</td><td> —</td><td>4C, 8G</td><td>3C, 4G</td>
<td>Compound of formula 45</td><td></td><td></td><td></td><td></td>
<td> 0,032</td><td> 0</td><td>2G</td><td> 0</td><td> 0</td>
<td> 0,125</td><td>2E, 7G</td><td>4E, 8G</td><td>8E, 9G</td><td>9C</td>
<td> 0,5</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
Table 7 cd
<td> 1</td><td> 2</td><td>3 'and</td><td> 1 <sup>4</sup></td><td> 1 <sup>5</sup></td>
<td>Compound of formula 44</td><td></td><td></td><td></td><td></td>
<td> 0,032</td><td>2G</td><td>2G</td><td>3G</td><td> 0</td>
<td> 0,125</td><td>10E</td><td>4E, 8G</td><td>8E, 8G</td><td>9C</td>
<td> 0,5</td><td>10E</td><td>10E</td><td>Loe</td><td>10C</td>
<td>Compound of formula 68</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,032</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,125</td><td>10E</td><td>10E</td><td>l; 0E</td><td>10C</td>
<td> 0,25</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 67</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>2C, 4G</td><td>2C, 7G</td><td>3C, 8G</td><td>5C, 7G</td>
<td> 0,032</td><td>3C, 6G</td><td>3G, 7G</td><td>3C, 7G</td><td>3C, 6G</td>
<td> 0,125</td><td>2C, 8G</td><td>3C, 8G</td><td>5E, 9G</td><td>8C</td>
<td> 0,5</td><td>2C, 8G</td><td>5E, 9G</td><td>5E, 9G</td><td>5C, 6C</td>
<td>Compound of formula 65</td><td></td><td></td><td></td><td></td>
<td> 0,004</td><td>8G</td><td>7G</td><td>8G</td><td>8C</td>
<td> 0,008</td><td>8G</td><td>8G</td><td>8G</td><td>9C</td>
<td> 0,016</td><td>8E, 9G</td><td>6E, 9G</td><td>8E, 9G</td><td>9C</td>
<td> 0,032</td><td>5E, 9G</td><td>8E, 9G</td><td>10E</td><td>10C</td>
<td>Compound of formula 64</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>IN</td><td>10E</td><td>9E, 9G</td><td>10C</td>
<td> 0,032</td><td>ilOE</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,125</td><td>ilOE</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,25</td><td>ilOE</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 63</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,032</td><td>ilOE</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,125</td><td>ilOE</td><td>10E</td><td>10E</td><td>10C</td>
<td> 0,25</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>Compound of formula 62</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>3G</td><td>4G</td><td>5G</td><td>3G</td>
<td> 0,032</td><td>7G</td><td>7G</td><td>7G</td><td>5C, 6G</td>
<td> 0,125</td><td>9G</td><td>9G</td><td>9G</td><td>10C</td>
<td>Compound of formula 61</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>2C, 5G</td><td>7G</td><td>7G</td><td>2C, 5G</td>
<td> 0,032</td><td>9G</td><td>10E</td><td>8E, 9G</td><td>9C</td>
<td> 0,125</td><td>10E</td><td>10E</td><td>IN</td><td>9C</td>
<td>Compound of formula 60</td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>8E, 9C</td><td>10E</td><td>IN</td><td>10G</td>
<td> 0,032</td><td>10E</td><td>l, 0E</td><td>10E</td><td>10C</td>
<td> 0,125</td><td>10E</td><td>Loe</td><td>1OE</td><td>10C</td>
Test G. In plastic pots, 10 cm in diameter, filled with Fallsington's sand and dust, containing about 1 / / of organic matter from soil in State Delawore, St. Ser. Am. or about 4% of the substance
126 541 organic soil from Illinois, St. Ser. Am., Cyprus (Cyperus rotundus) tubers were planted, 5 pieces in a pot. The compounds listed in Table 8 were applied to the surface of the earth or to the tubers and soil next to them, or by mixing the compounds with the soil. When applied to the surface, the compound was sprayed onto the formed surface of the soil after planting the tubers, when used on the tubers, the compound was sprayed onto the tubers and the soil next to them, taria viridis), ground grass (Agropyron repens), resin (Lolium multiflorum) and rigid base (Bromus rigidus) .
In the second trough, the European knotweed (Poly, 3 gonum convolvulus), the warp (Kochia scoparia), the knotweed (Polygonum pensylvaniicum), the common chamomile (Matricaria inodora), the stulisz (Sisymbrium altissium), mustard (Desicula stica) pinnata), amaranth (Amaran Table 8
Trials with ciboTa, results after 4 weeks
<td rowspan="2">Formula of the compound used in the compound quantity in kg / ha</td><td colspan="3">Spraying on the ground with an organic content</td><td colspan="2">Spraying on tubers and soil with an organic content</td><td colspan="2">Mixing with soil with organic matter content</td>
<td colspan="2">little girl</td><td>large</td><td>small</td><td>large</td><td>small</td><td>large</td>
<td>Formula 39</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>10E</td><td></td><td>4C, 7G</td><td>10E</td><td>7E, 9G</td><td>10E</td><td>8E, 9G</td>
<td> 0,016</td><td>10E</td><td></td><td>8E, 8G</td><td>10E</td><td>10E</td><td>10E</td><td>8E, 9G</td>
<td> 0,032</td><td>10E</td><td></td><td>9E, 9G</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td>Formula 41</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td> 0,008</td><td>5C, 8G</td><td></td><td> 0</td><td>9E, 9G</td><td>5E, 7G</td><td>8E, 9C</td><td>2C, 3G</td>
<td> 0,016</td><td>9E, 9G</td><td></td><td>2C, 4G</td><td>10E</td><td>10E</td><td>9E, 9C</td><td>3C, 3G</td>
<td> 0,032</td><td>10E</td><td></td><td>10C</td><td>10E</td><td>9E, 10C</td><td>10C</td><td>7E, 3C, 8G</td>
then the tubers were covered with a layer of soil, and when mixed with soil, the tubers were covered with a layer of soil mixed with the test compound.
Immediately after treatment, the pots were sprayed with water, imitating 0.3 cm of water fall within 90 minutes, after which they were placed in ciefplarmi. The results observed after 4 weeks are given in Table 8. They testify to the high activity of the tested compounds in relation to cyprus.
Test H. Two troughs with a diameter of 25 cm made of plastic and lined with polyethylene were filled with Fallsington's sand and dust. In one basin, wheat (Triticum aestirum), barley (Hordeum vulgare), deaf oat (Avena fatua), roof pod (Bromus tecterum), rye pod (Bromus secalinus), field fox (Alopecurus myosuroides), plantain , trichinosis (Sethus retroflexua) and spine brine (Solsola kall). 33 Both troughs described above were tested before emergence of plants, and at the same time two troughs with the same plants were used for post-emergence testing, namely when the plants, depending on their type, had a height of 1-15 cm. The test compounds were dissolved in a non-poisonous solvent and the solution was poured into pans. At the same time, plants were bred in separated basins under the same conditions and some of them were treated with solvent only, and the remaining ones were not treated.
All troughs were kept in the greenhouse and after
20 days were evaluated visually. These results, given in Table 9, show that many compounds of formula I can be used to selectively control weeds in wheat and barley crops.
Table 9
<td rowspan="2">Plants tested</td><td colspan="2">Test compound with formula 39 and the amount of this compound in kg / ha</td><td colspan="2">Test compound of formula 39 and the amount of this compound in kg / ha</td><td colspan="3">Test compound of formula 65 and amount of this compound in kg / ha</td>
<td> 1/16</td><td> 4/8</td><td> 1/16</td><td> 1/8</td><td> 1/64</td><td> 1/32</td><td> 1/16</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td><td> 8</td>
<td>Before leaving</td><td></td><td></td><td colspan="2">After rising</td><td colspan="3">Before leaving</td>
<td>Wheat</td><td>9E, 9G</td><td>9E, 9G</td><td>9C</td><td>| IOC</td><td>P</td><td> 0</td><td> 0</td>
<td>Barley</td><td>7H, 8G</td><td>8H, 8G</td><td>9C</td><td>IOC</td><td> 0</td><td> 0</td><td> 0</td>
126 541
table cd 9 ι | 2 | 3 | 4 | 5 | β | 7 | 8
<td>Deaf oats</td><td>4H, 7G</td><td>TH, 8G</td><td>9C</td><td>IOC</td><td>fi</td><td> 0</td><td> , 0</td>
<td>Roof crock</td><td>9 9Ξ, 9G</td><td>10E</td><td>IOC</td><td>IOC</td><td> 0</td><td> 0</td><td>IG</td>
<td>Rye stock</td><td>7G, 8G</td><td>9E, 9G</td><td>IOC</td><td>IOC</td><td> 0</td><td> 0</td><td>IG</td>
<td>Fieldcleaner</td><td>5H, 8G</td><td>8H, 9G</td><td>IOC</td><td>10C</td><td> 0</td><td> 0</td><td>2G</td>
<td>Panicle annual</td><td>5C, 7G</td><td>7C, 8G</td><td>10C</td><td>10C</td><td> 0</td><td> 0</td><td>IG</td>
<td>fretsaw</td><td>8C, 8G</td><td>8C, 9G</td><td>10C</td><td>IOC</td><td> 0</td><td> 0</td><td>IG</td>
<td>Proper wash</td><td>5H, 7G</td><td>7H, 8G</td><td>IOC</td><td>IOC</td><td> 0 <sub>X</sub></td><td> 0</td><td> 0</td>
<td>Darnel</td><td>6H, 7G</td><td>8H, 8G</td><td>10C</td><td>10C</td><td> 0</td><td> 0</td><td> 0</td>
<td>Stokłosa stiff</td><td>8C, 9G</td><td>10C</td><td>IOC</td><td>10C</td><td> 0</td><td> 0</td><td> 0</td>
<td>Clam Knotweed</td><td>4C, 7G</td><td>5C, 8G</td><td>IOC</td><td>IOC</td><td>3C, 5G</td><td>7C, 8G</td><td>7C, 8G</td>
<td>Mietelnik</td><td>9C, 9G</td><td>8C, 9G</td><td>IOC</td><td>10C</td><td>5C, 7G</td><td>7C, 8G</td><td>9C</td>
<td>Water pepper</td><td>7C, 8G</td><td>9C, 9G</td><td>IOC</td><td>IOC</td><td>4C, 7G</td><td>, 10C</td><td>10C</td>
<td>Chamomile</td><td>9C, 9G</td><td>SC, 9G</td><td>IOC</td><td>IOC</td><td>9G</td><td>9G</td><td>9G</td>
<td>sisymbrium</td><td>10C</td><td>10C</td><td>IOC</td><td>10C</td><td>10C</td><td>IOC</td><td>IOC</td>
<td>Mustard</td><td>8C, 8G</td><td>9C, 9G</td><td>IOC</td><td>10C</td><td><sub>(</sub>10C</td><td>10C</td><td>IOC</td>
<td>Stulicha bitch</td><td>10C '</td><td>10C</td><td>10C</td><td>10C</td><td>7C, 9G</td><td>, 10C</td><td>IOC</td>
<td>amaranth</td><td>8C, 9G</td><td>, ioc</td><td>10C</td><td>10C</td><td>7G</td><td>5C, 8G</td><td>IWC</td>
<td>Spiky brine</td><td>7C, 7G</td><td>8C, 8G</td><td>10C</td><td>10C</td><td>3G</td><td>4G</td><td>7C, 5G</td>
table 9 cd
<td rowspan="2">Plants tested</td><td colspan="3">Test compound of formula 65 and amount of this compound in kg / ha</td><td colspan="3">Test compound of formula 106 and the amount of this compound in kg / ha</td><td colspan="3">Test compound of formula 106 and amount of this compound in kg / ha</td>
<td> 1/64</td><td> 1 1/32</td><td> | 1/16</td><td> 1/64</td><td> | 1/32</td><td> 1 1/16</td><td> 1/64</td><td> 1 1/32</td><td> 1 1/16</td>
<td>After rising Wheat</td><td><sup>0</sup></td><td> 0</td><td>IC</td><td>prs 0</td><td>sed up 0</td><td>moths 0</td><td> 1 0</td><td>about to come up and</td><td>and in IC</td>
<td>Barley</td><td> 0</td><td>about</td><td>and</td><td> 0</td><td>IG</td><td>IG</td><td> , 0</td><td> > 0</td><td> ' 0</td>
<td>Deaf oats</td><td>lo</td><td> 0</td><td>IC</td><td> 0</td><td>2G</td><td>3G</td><td> 0</td><td> 0</td><td>2C</td>
<td>Roof crock</td><td> 0</td><td> 0</td><td> 0</td><td>IG</td><td>3G</td><td>5G</td><td> \ 0</td><td> 0</td><td>2G</td>
<td>Rye stock</td><td>this</td><td> 0</td><td> 0</td><td>IC, 2G</td><td>IC, 3G</td><td>2C, 4G</td><td> 0</td><td> ! 0</td><td>IC, 2G</td>
<td>Fieldcleaner</td><td> 0</td><td> 0</td><td> 0</td><td>2G</td><td>3G</td><td>4G</td><td> 0</td><td> 0</td><td>2G</td>
<td>Panicle annual</td><td> 10</td><td> 0</td><td>2G</td><td>2G</td><td>3G</td><td>5G</td><td> 0</td><td> 0</td><td>3G</td>
<td>fretsaw</td><td>IC</td><td>IC</td><td>2C, 3G</td><td><sub>(</sub> 0</td><td> 0</td><td>IG</td><td> , 0</td><td>IC</td><td>3C</td>
<td>Proper wash</td><td> 0</td><td> 0</td><td> 0</td><td>, θ</td><td> 0</td><td>. 2G</td><td> 1 0</td><td> 0</td><td>IG</td>
<td>Darnel</td><td> 0</td><td> 0</td><td> 0</td><td> ' 0</td><td>2G</td><td>3G</td><td> 0</td><td> 0</td><td>2G</td>
<td>Stokłosa stiff</td><td> 0</td><td> 0</td><td> : 0</td><td>; about</td><td> ; 0</td><td> 0</td><td> , 0</td><td> 0</td><td> 0</td>
<td>Clam Knotweed</td><td>9C</td><td>IOC</td><td>IOC</td><td>9C</td><td>9C</td><td>10C</td><td>IOC</td><td>Ilocano</td><td>10C</td>
<td>Mietelnik</td><td>IOC</td><td>'łoc</td><td>IOC -</td><td>9C</td><td>IOC</td><td>IOC</td><td>, 1K "C</td><td>IOC</td><td>IOC</td>
<td>Water pepper</td><td>'9C</td><td>9C</td><td>IOC</td><td>9C</td><td>ipc</td><td>IOC</td><td>HOC</td><td>IOC</td><td>IOC</td>
<td>Chamomile</td><td>IOC</td><td>IOC</td><td>IOC</td><td>9G</td><td>9G</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>sisymbrium</td><td>~ 10C</td><td>IOC</td><td>IOC</td><td>10C</td><td>10C</td><td>'10C</td><td>night</td><td>IOC</td><td>IOC</td>
<td>Mustard</td><td>~ 10C</td><td>IOC</td><td>IOC</td><td>10C</td><td>10C</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Stulicha bitch</td><td>IOC</td><td>IOC</td><td>IOC</td><td>10C</td><td>night</td><td>IOC</td><td>night</td><td>aoc</td><td>IOC</td>
<td>amaranth</td><td>9C</td><td>IOC</td><td>IOC</td><td>8C</td><td>9C</td><td>10C</td><td>IOC</td><td>, 10C</td><td>10C</td>
<td>Spiky brine</td><td>9C 1</td><td>IOC</td><td>IOC</td><td>3C, 5G</td><td>7C, 7G</td><td>8C, 8G</td><td>IOC</td><td>FLOC</td><td>IOC</td>
t
Trial I. Plastic pots with a diameter of about 13 cm on / full with a 1: 1 mixture of FaUłsington's silty soil and sand, and the following plants were planted in them, one species in each of the pots: moraine (Morrenia odorata), plantain (Plantago spp.), burdock (Arcitium • 0 minus), field bindweed (Convolvulus arvensis), dandelion (Taraxacum officenale), psdanka (Solanum carolinense), canine tooth (Cynodon dactylon), proper mole (Agropyron repens), dallis grass (Paspalum dilatutum), and wild sorghum (Sorghum habepense).
AND
126 541
The pots were placed in a greenhouse and the plants were grown within a few weeks. The test compound was dissolved in a harmless solvent and the solution was sprayed onto the leaves. For comparative purposes, the same plants were grown without treatment with a solution or only with a solvent treatment. The results were visually evaluated after 1 and 8 weeks. These results, given in Table 10, show that the test compound has a strong herbicidal effect on broad-leaved weeds and perennial weeds.
Table 10
<td rowspan="3">examined plants</td><td colspan="4">Test compound of formula 39 and the amount of this compound</td>
<td colspan="2">After 1 week</td><td colspan="2">After 8 weeks</td>
<td colspan="2">1/8 kg / ha | l / 4 kg / ha</td><td colspan="2">1/8 kg / hajl / 4 kg / ha</td>
<td>Morenia</td><td> 0</td><td> 0</td><td>10C</td><td>10C</td>
<td>Grandmother</td><td> 0</td><td> 0</td><td>10C</td><td>10C</td>
<td>Burdock</td><td> 0</td><td> 0</td><td>4C</td><td>10C</td>
<td>Bindweed field</td><td> 0</td><td>2C</td><td>7C</td><td>8C</td>
<td>puffball</td><td> 0</td><td> 0</td><td>10C</td><td>10C</td>
<td>nightshade</td><td> , 0</td><td>1C</td><td>5C</td><td>10C</td>
<td>Dog's proper tooth</td><td>5C</td><td>6C</td><td>5C, 7G</td><td>6C, 8G</td>
<td>Perz appropriate</td><td>6C</td><td>7C</td><td>10C</td><td>10C</td>
<td>Grass dellys</td><td>6C</td><td>Joc</td><td>8C, 8G</td><td>10C</td>
<td>Wild sorghum</td><td>8C</td><td>9C</td><td>10C</td><td>10C</td>
Test J. Strongly the herbicidal effect of one of the compounds of formula I was confirmed by the results of field tests. The test compound was applied before emergence of the plants on the silty-sandy soil and after 3 days the field was irrigated by supplying water in an amount corresponding to a 2.5 cm layer. After 4 weeks, the weed control was calculated as a percentage. The results are given in Table 11.
Table 11
<td rowspan="2">examined plants</td><td colspan="5">Test compound of formula 39 and the amount of this compound in kg / ha</td>
<td>no trak- accompanied Well</td><td> 0,31</td><td> 0,063</td><td> 0,125</td><td> 0,25</td>
<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td>
<td>crabgrass</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> >100</td>
<td>fretsaw</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td>Ϊ0 (ί</td>
<td>cyprus</td><td> 0</td><td> 93</td><td> 100</td><td> 100</td><td> 100</td>
<td>amaranth</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Pożybyt</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Velvetleaf Avicenna</td><td> 0</td><td> 98</td><td> 98</td><td> 100</td><td> 100</td>
| 2 3 and 4 | 5 and 6
<td>Pigweed White</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> ,100</td>
<td>Purslane common</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>water pepper ostrogorzki</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>barnyardgrass one sided</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Darnel</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> ,100</td>
<td>Oat deaf</td><td> 0</td><td> 98</td><td> 100</td><td> 100</td><td> 100</td>
<td>Spinach</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Flax</td><td> 0</td><td> 90</td><td> 100</td><td> 100</td><td> 100</td>
<td>Chicory Dining Area</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Cabbage</td><td> 0</td><td> /160</td><td> 100</td><td> 100</td><td> 100</td>
<td>Beetroot red</td><td> 0</td><td> 160</td><td> 100</td><td> .100</td><td> 100</td>
<td>Carrot</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Bean climbing</td><td> 0</td><td> . 50</td><td> 60</td><td> 70</td><td> . 90</td>
<td>Bean beans</td><td> 0</td><td> 80</td><td> 90</td><td> 95</td><td> 100</td>
<td>Tomato</td><td> 0</td><td> 100</td><td> 100</td><td> 400</td><td> ,100</td>
<td>Nut terrestrial</td><td> 0</td><td> 70</td><td> 30</td><td> 90</td><td> 90</td>
<td>Potato</td><td> 0</td><td> 90</td><td> 90</td><td> 100</td><td> 100</td>
<td>Cucumber</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Pumpkin</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Beetroot sugar</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Soy</td><td> 0</td><td> 90</td><td> 95</td><td> 98</td><td> 98</td>
<td>Lucerne</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Shamrock</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>
<td>Shamrock Japanese</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td><td> ,100</td>
<td>Cotton</td><td> 0</td><td> 80</td><td> 90</td><td> 90</td><td> 95</td>
<td>Oat</td><td> 0</td><td>| l00</td><td> 100</td><td>device The number</td><td> ,100</td>
<td>Okra</td><td> 0</td><td> 90</td><td> ~? 90</td><td> 160</td><td> 100</td>
<td>Rice</td><td> . 0</td><td> 100</td><td> 400</td><td> 1/00</td><td> 100</td>
<td>Wheat</td><td> 0</td><td> 90</td><td> /100</td><td>1P0</td><td> 100</td>
<td>Sorghum</td><td> 0</td><td> 100</td><td> 160</td><td>and after</td><td> 100</td>
<td>Maize</td><td> 0</td><td> 160</td><td> (160</td><td>l (00</td><td> 100</td>
<td>sunflower</td><td> 0</td><td> 70</td><td> 90</td><td> 95</td><td> 400</td>
<td>safflower</td><td> 1 0</td><td> 100</td><td> 100</td><td> 100</td><td> 400</td>
Test K. This test showed the effect of the compound used in test J on nuisance weed species when treated with this compound after emergence of plants. The test was carried out in a field, about 30 days before mowing, when the mixed plants were about 15 cm high. The test compound was used in an aqueous solution with the addition of 0.2% surfactant in the form of WK preparation. 500 liters of solution were used on 1 ha and each treatment was repeated three times.
Within 4 days after treatment a rainfall of 5 cm was recorded and before the assessment, that is within 16 weeks of the procedure, the rainfall was still 37 cm. The results observed 16 weeks after the procedure are given in Table 12. These are the results determined as the average as a percentage compared to the control.
Table 12
Weed control expressed as a percentage
<td rowspan="2">Weeds tested</td><td colspan="4">Test compound of formula 39 and the amount of this compound kg / ha</td>
<td>attempt kontrol- on</td><td> 0,5</td><td>and o</td><td> 1 /2,0</td>
<td>Generally</td><td> 6</td><td> 81</td><td> 90</td><td> 94</td>
<td>grass</td><td> 0</td><td> 81</td><td> 84</td><td> 93</td>
<td>broadleaved</td><td> 0</td><td> 91</td><td> 96</td><td><sup>98</sup></td>
<td>Long-haired clover</td><td> 0</td><td> 73</td><td> 80</td><td> 92</td>
<td>Hairy monkey</td><td> 0</td><td>7T "</td><td> 73</td><td> 86</td>
<td>Goldenrod</td><td> 0</td><td> 100</td><td> 100</td><td> 100</td>
<td>Blackberry dewberry</td><td> 0</td><td> 97</td><td>Χ00</td><td> 100</td>
<td>Poison Sumac</td><td> 0</td><td> 67</td><td> 85</td><td> 95</td>
On | 1 m<sup>2</sup> in the untreated field, these plants appeared on average in the following numbers:
Long-clover clover 7.5
Hairy breakthrough 7.5
Goldenrod 10.8
Dewberry 5.4
Poisonous sumac 10.8
Contents4
2 sheets
Sheet 1 Sheet 2
97 members in 31 offices
Priority claims16
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|---|---|---|---|
| 91096578 | United States of America | A | |
| 91096578 | United States of America | A | |
| 96507078 | United States of America | A | |
| 96507078 | United States of America | A | |
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| 1978910965 | – | – | – |
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Numbers
- Publication, DOCDB
- 126541
- Publication, EPODOC
- PL126541B
- Application
- 215949
- Application, DOCDB
- 21594979
- Application, EPODOC
- PL19790215949
Titles
- English
- AGENT FOR FIGHTING AGAINST UNDESIRABLE PLANTS
Classification
- CPC, 19
- C07C311/65
- A01N47/28
- A01N47/36
- C07C317/00
- C07C323/00
- C07D239/42
- C07D239/46
- C07D239/47
- C07D239/48
- C07D239/52
- C07D251/14
- C07D251/16
- C07D251/18
- C07D251/46
- C07D251/52
- C07D253/06
- C07D253/07
- C07D253/075
- C07D521/00
- IPC, 26
- A01N
- A01N41 00
- A01N47 28
- A01N47 36
- C07C311 65
- C07D
- C07D239 42
- C07D239 46
- C07D239 47
- C07D239 48
- C07D239 52
- C07D239 69
- C07D251 14
- C07D251 16
- C07D251 18
- C07D251 22
- C07D251 42
- C07D251 46
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