CA1168056A - Weed-killer composition containing amides as antidotes for alpha-halo-acetanilides - Google Patents
Weed-killer composition containing amides as antidotes for alpha-halo-acetanilidesInfo
- Publication number
- CA1168056A CA1168056A CA000413740A CA413740A CA1168056A CA 1168056 A CA1168056 A CA 1168056A CA 000413740 A CA000413740 A CA 000413740A CA 413740 A CA413740 A CA 413740A CA 1168056 A CA1168056 A CA 1168056A
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- CA
- Canada
- Prior art keywords
- formula
- composition
- compound
- weed
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
Abstract
ABSTRACT OF THE DISCLOSURE
Selective weed-killer composition for use in agricult-ure, containing an antidote with formula:
where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylaniline; R2 is hydrogen, alkyl, haloalkyl, haloalkenyl, alkinyl, phenyl; the alipha-tic radicals having 1-4 atoms of carbon and the halogens chlorine or bromine; or also R1 and R2 may form a ring structure type piperidyl, alkyl-piperidyl, morpholyl, alkyl-morpholyl, hexamethylenemine, oxazolidine, 5-alkoxy-methyl--2,2-dimethyl-oxazolidine; together with a weed-killer com-position with formula:
where R1 and R2 are alkyl with 1-4 atoms of carbon; A is -CH2-; -CH2-CH2-;
Selective weed-killer composition for use in agricult-ure, containing an antidote with formula:
where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylaniline; R2 is hydrogen, alkyl, haloalkyl, haloalkenyl, alkinyl, phenyl; the alipha-tic radicals having 1-4 atoms of carbon and the halogens chlorine or bromine; or also R1 and R2 may form a ring structure type piperidyl, alkyl-piperidyl, morpholyl, alkyl-morpholyl, hexamethylenemine, oxazolidine, 5-alkoxy-methyl--2,2-dimethyl-oxazolidine; together with a weed-killer com-position with formula:
where R1 and R2 are alkyl with 1-4 atoms of carbon; A is -CH2-; -CH2-CH2-;
Description
WEEn-lCILLER COMPOSI[ION CONTAINING AhlIDES AS ANTIDOT~S FOR
ALPIIA-HALO~CETANALIDES
The use of weed-killers in agriculture is an agronomie S necessity which saves heavy manual and mechanical processes.
~; llowever, the weed-killers presently avail.able are not completely effective against the tou~hest weeds, or, if effective, often phytotox:ic for the crops involved.
. The pllrpose of this invention is therefore to permit 10 the use in-agriculture, particularly in f.iel.ds of maize and sorghum of some weed-ki]l.ers of the alpha-halo-acetanilide ,, classes normally phytotoxic on crops, bllt very effective towards :infested grass more resistant to other weed-kil-`~ lers, through the preparation of new weed-lciller compo-. ~ . .
: 15 sitions containin~ such alpha hal.o-acetanalides together w:ith spee:iEic am:ides highly effective in redl1eing or elimi-~` nating phytoxi.city Por the ma;æe or sorghl1m ("ant.idotic : effect"). The use of al~ les as antidotes for th.iolcarbamate or triaz.inic ~ecd-lc.i.:Llers, deser-ibed in U.S.A. Patent No.
4.021.224 - wh.ieh cloes not, howeve~r, mention the poss.ibili-ty of us.irl~ these ami~les as ant:idotes for other weed-kil-; lers - is already Icnown in teehni~ue.
In Ital.ian Patent Applications Nos. 28.867 A/76 and 31.189 A/77 deseriptions are given of some diehloroaeetami-des as ester anti.(lotes of the subs-ti.tuted N,N- glyeine, whieh di.ffer from the alpha-halo-acetanalides for the pre-sence in the:ir moleeule of different funetional ~roups as well as for biologieal pro~erties.
~ The present invention provides a solution, whieh dif-: 3 fers from that indicated above, as :it foresees the prepara-tion of~ a seleetive weed-lcil]er eompos:ition for maize and sorghum eontaining alpha-halo aeetanili.des of formu]a:
,' ~
\
I 1 6$0~
~ ~ N ~ A-O R3 (I) ~ R2 \ 2 where R1 and R~ are al.kyl w;th i-4 atoms of carbon; A is
ALPIIA-HALO~CETANALIDES
The use of weed-killers in agriculture is an agronomie S necessity which saves heavy manual and mechanical processes.
~; llowever, the weed-killers presently avail.able are not completely effective against the tou~hest weeds, or, if effective, often phytotox:ic for the crops involved.
. The pllrpose of this invention is therefore to permit 10 the use in-agriculture, particularly in f.iel.ds of maize and sorghum of some weed-ki]l.ers of the alpha-halo-acetanilide ,, classes normally phytotoxic on crops, bllt very effective towards :infested grass more resistant to other weed-kil-`~ lers, through the preparation of new weed-lciller compo-. ~ . .
: 15 sitions containin~ such alpha hal.o-acetanalides together w:ith spee:iEic am:ides highly effective in redl1eing or elimi-~` nating phytoxi.city Por the ma;æe or sorghl1m ("ant.idotic : effect"). The use of al~ les as antidotes for th.iolcarbamate or triaz.inic ~ecd-lc.i.:Llers, deser-ibed in U.S.A. Patent No.
4.021.224 - wh.ieh cloes not, howeve~r, mention the poss.ibili-ty of us.irl~ these ami~les as ant:idotes for other weed-kil-; lers - is already Icnown in teehni~ue.
In Ital.ian Patent Applications Nos. 28.867 A/76 and 31.189 A/77 deseriptions are given of some diehloroaeetami-des as ester anti.(lotes of the subs-ti.tuted N,N- glyeine, whieh di.ffer from the alpha-halo-acetanalides for the pre-sence in the:ir moleeule of different funetional ~roups as well as for biologieal pro~erties.
~ The present invention provides a solution, whieh dif-: 3 fers from that indicated above, as :it foresees the prepara-tion of~ a seleetive weed-lcil]er eompos:ition for maize and sorghum eontaining alpha-halo aeetanili.des of formu]a:
,' ~
\
I 1 6$0~
~ ~ N ~ A-O R3 (I) ~ R2 \ 2 where R1 and R~ are al.kyl w;th i-4 atoms of carbon; A is
2 ; 2 l2 ; -ICll-CH2-; R3 ~.s alkyl with 1-4 atoms of carbon; and X may be chlorine or bromine, in which amides wi-th the following formula are aclded as antidotes for said alpha-halo-acetanilide antidotes having the formula:
o /Kl R-C-N'~ (II) \R2 where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylanil.ine; R2 is hydrogen, : 15 ~al.kyl, haloalkyl, haloalkenyl, allcinyl, phenyl; the alipha-tic radicals being w.ith 1-4 atoms oE carbon and the halo-~ens ehlorine or bromine; or also R1 and R2 may Eorm a ring s-trueture type pi.per:icly:l., allcylp:iper:iclyl, morpholy1., alkyl-morpllolyl, hexamethy:Lene~ltllne, oxazo:l:i.d.ine, 2,2-dime-thyl-o.xazol:icl:i.ne, 5-alkox:i.-metllyl-2,2-dimethyl-oxazolicil.ne.
The amides oE form~lla (II) may be producecl with known metllods, :Eor example by condens.lt:ion of a haloalkylchlorine with an appropriate amine, in the presence of an acceptor of hydroehlorie aeid, whiell may even be an excess of amine.
This reaetion may take plaee in solvent, preferably at low temperature.
: ~ Among the amides of formula (II) of the present i.nven-; tion we fi.nd in parti.cular the di-haloacetamides of formula:
~W
O C~l-C=C /
CIlX -C-N / I \ Z (III) R
where X and Z are chlorine or bromine, Y ancl W hycirogen, I J 6~056 ." ~ . , ch].orine or bromine, R is hy(lro6en allcyl, llaloakyl~ alke-nyl, haloal.kenyl, alkinyl, haloalkinyl, these radicals hav-. ing 1-3 ~toms of carbon.
Fifty-ei.gllt preferred compounds of formula (II) accord-05 ing to the present invention are l:isted i.n the fol.lowin~
Table 1, in which the last thirty-six compounds are, i.n `: particular, comp~urlds of formula (III).
Table 1 10 Compounds R-C-N < Rl (II) ' N. R R R
. 1. . CI~Cl2- -CII-CI~ 2 3 .. ~ 2. CIICl2- 2 3 -C112-C1l2-CH3 CIICl.2- -Cl-12-CII=CI-l2 -C~l-C~I -4 CIIC] -CII-CII ( 3)2 : 5- C}ICl2- -C112-CI-l3 ~
6. C~IC12- -Cll-C~I -C~12-ClICl-CIl2Cl 7- Cl-lCl2- -C~l-CII -C~12-CCl=Cll2 8. C~ICl2- -Cll2-CIICl-C112Cl -Cl-12C~ICl-C112Cl 9. C~ICl2- -Cll2-CCl=C}I~ -C~l-CCl=C112 10. Cll C:1.2- -Cll -CII=CII -Cll-CIICl=CH2 1 1 . Cll C12- -Cl-12-C112-C~13 -C112-Cl-12-C~13 12. CIIC12- C2~
: 2 ~C1l2-Cll2-C,~12 30 14. CllCl2- ~Cll-CII ~
15. Cl-l cl2_ ~C112 Cll~
16. C~ICl2- ~C 2 0 2
o /Kl R-C-N'~ (II) \R2 where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylanil.ine; R2 is hydrogen, : 15 ~al.kyl, haloalkyl, haloalkenyl, allcinyl, phenyl; the alipha-tic radicals being w.ith 1-4 atoms oE carbon and the halo-~ens ehlorine or bromine; or also R1 and R2 may Eorm a ring s-trueture type pi.per:icly:l., allcylp:iper:iclyl, morpholy1., alkyl-morpllolyl, hexamethy:Lene~ltllne, oxazo:l:i.d.ine, 2,2-dime-thyl-o.xazol:icl:i.ne, 5-alkox:i.-metllyl-2,2-dimethyl-oxazolicil.ne.
The amides oE form~lla (II) may be producecl with known metllods, :Eor example by condens.lt:ion of a haloalkylchlorine with an appropriate amine, in the presence of an acceptor of hydroehlorie aeid, whiell may even be an excess of amine.
This reaetion may take plaee in solvent, preferably at low temperature.
: ~ Among the amides of formula (II) of the present i.nven-; tion we fi.nd in parti.cular the di-haloacetamides of formula:
~W
O C~l-C=C /
CIlX -C-N / I \ Z (III) R
where X and Z are chlorine or bromine, Y ancl W hycirogen, I J 6~056 ." ~ . , ch].orine or bromine, R is hy(lro6en allcyl, llaloakyl~ alke-nyl, haloal.kenyl, alkinyl, haloalkinyl, these radicals hav-. ing 1-3 ~toms of carbon.
Fifty-ei.gllt preferred compounds of formula (II) accord-05 ing to the present invention are l:isted i.n the fol.lowin~
Table 1, in which the last thirty-six compounds are, i.n `: particular, comp~urlds of formula (III).
Table 1 10 Compounds R-C-N < Rl (II) ' N. R R R
. 1. . CI~Cl2- -CII-CI~ 2 3 .. ~ 2. CIICl2- 2 3 -C112-C1l2-CH3 CIICl.2- -Cl-12-CII=CI-l2 -C~l-C~I -4 CIIC] -CII-CII ( 3)2 : 5- C}ICl2- -C112-CI-l3 ~
6. C~IC12- -Cll-C~I -C~12-ClICl-CIl2Cl 7- Cl-lCl2- -C~l-CII -C~12-CCl=Cll2 8. C~ICl2- -Cll2-CIICl-C112Cl -Cl-12C~ICl-C112Cl 9. C~ICl2- -Cll2-CCl=C}I~ -C~l-CCl=C112 10. Cll C:1.2- -Cll -CII=CII -Cll-CIICl=CH2 1 1 . Cll C12- -Cl-12-C112-C~13 -C112-Cl-12-C~13 12. CIIC12- C2~
: 2 ~C1l2-Cll2-C,~12 30 14. CllCl2- ~Cll-CII ~
15. Cl-l cl2_ ~C112 Cll~
16. C~ICl2- ~C 2 0 2
3 3 ' ~ \
1 1 ~gO5~
.
17. C11 Cl2- ,CI-12-,cll-c112-ocll(c~l3)2 . C l3 ~C1-13 ; 18. CC13- ~(~,11 -C~l-CII -OC11(C~-I ) : C113 ~C113 .. ` 05 19. C112Br.C}113r- ~Cll2-~cll-cl 2 3 Cll Cll 20. Cll C12- ~C112-,CII-C112-0-C113 - C1~l3\C113 21. C11 C12- ~C112-CI-1-CH2-0-C}12 C 2 " Cll ~C~l ' 22. C11213r.CI-113r- ~C112-~11-C~12-0-C112-CI~=C112 : ~ C~113\C113 Co111polm~1s C C ~ 2 1 <;~ (Ill) : R
; ~ Y ~I Z 1~ , ~; 23 Cl ~I C1 Cl -C113 2 24 Cl I I Cl Cl ~CI I -C~l C1 11 C1 Cl -C112-C112-CI-13 26 Cl 11 Cl Cl -~ C113 27 C1 1 1 C1 Cl -C112-C~I=C1 12 28 C1 H Cl. C1 ( 3 2 2 5 29 Cl 11 C]. Cl -C112-C~I=CC12 C]. Cl C1 C1 -c~l3 31 Cl C1 Cl Cl -C112-CH3 32 Cl Cl C1 Cl -Cll~cll3 33 . Cl C1 C1 Cl -C112-CII=C112 34 Cl Cl Cl Cl ( ~ ) 2 Cl Cl C1 Cl -C1~2-CCl=CC12 36 Cl Cl 11 C1 ~ C 12 C 3
1 1 ~gO5~
.
17. C11 Cl2- ,CI-12-,cll-c112-ocll(c~l3)2 . C l3 ~C1-13 ; 18. CC13- ~(~,11 -C~l-CII -OC11(C~-I ) : C113 ~C113 .. ` 05 19. C112Br.C}113r- ~Cll2-~cll-cl 2 3 Cll Cll 20. Cll C12- ~C112-,CII-C112-0-C113 - C1~l3\C113 21. C11 C12- ~C112-CI-1-CH2-0-C}12 C 2 " Cll ~C~l ' 22. C11213r.CI-113r- ~C112-~11-C~12-0-C112-CI~=C112 : ~ C~113\C113 Co111polm~1s C C ~ 2 1 <;~ (Ill) : R
; ~ Y ~I Z 1~ , ~; 23 Cl ~I C1 Cl -C113 2 24 Cl I I Cl Cl ~CI I -C~l C1 11 C1 Cl -C112-C112-CI-13 26 Cl 11 Cl Cl -~ C113 27 C1 1 1 C1 Cl -C112-C~I=C1 12 28 C1 H Cl. C1 ( 3 2 2 5 29 Cl 11 C]. Cl -C112-C~I=CC12 C]. Cl C1 C1 -c~l3 31 Cl C1 Cl Cl -C112-CH3 32 Cl Cl C1 Cl -Cll~cll3 33 . Cl C1 C1 Cl -C112-CII=C112 34 Cl Cl Cl Cl ( ~ ) 2 Cl Cl C1 Cl -C1~2-CCl=CC12 36 Cl Cl 11 C1 ~ C 12 C 3
4 -` ~
: 1 ~ 6~n~6 .
. 37 C1 Cl 1~ Cl -C~1 C113 38 Cl C~. 11 C~ -C1~2-C~1=C}12 39 Cl Cl 11 Cl ( 3)2 Cl Cl 11 Cl -C112-CCl=C11Cl 05 41 C1 }1 11 Cl -C11-C1~
` 42 Cl 11 11 Cl C112 2 43 Cl 11 ~1 Cl ( 3)2 44 Cl 11 11 C~. -C1-12-C~1=C1~C1 Br }1 Cl Cl -C11-C11 lO 46 Br H C1 C1 -CH -C11=C1{
47 Br 11 Cl Cl ( 3)2 48 Br 11 Cl Cl -CH2-CH=CC12 49 ~r C1 C1 Cl -C}1-CH
}3r Cl Cl C1 -C112-C11=C112 15 51 13r Cl C1 Cl C(C}13)2 52 Br Cl Cl. Cl -C}12-CCl=CC12 53 Cl 11 Br 13r -C11-C11 54 Cl 11 Br 13r -C112-CH=C}12 Cl H Br }3r ( 3)2 56 C1 11 13r Br ~C112-C11=C13r2 57 Cl Br Br 13r 2 3 58 . Cl nr nr 13r -C112-C13r=CBr2 The invention also considers as preferretl weed-killer compounds of Eormula (I) those lis-tetl in the following Table 2.
Table 2 Compounds ~ N < 3 O
3o N. X ~ R1 R2 A_ 3 l. Cl -Cll3 2 3 -C!-12- 2 3 2. C1 -Cll3 2 3 -C112- -C}1(C~3)2 1 3 ~8056 .
.: .
: ; 3. Cl. -C1~3 2 3 -C~ - -c~3 4. Cl -C~1-C113 -C112- -C11(C~13)2
: 1 ~ 6~n~6 .
. 37 C1 Cl 1~ Cl -C~1 C113 38 Cl C~. 11 C~ -C1~2-C~1=C}12 39 Cl Cl 11 Cl ( 3)2 Cl Cl 11 Cl -C112-CCl=C11Cl 05 41 C1 }1 11 Cl -C11-C1~
` 42 Cl 11 11 Cl C112 2 43 Cl 11 ~1 Cl ( 3)2 44 Cl 11 11 C~. -C1-12-C~1=C1~C1 Br }1 Cl Cl -C11-C11 lO 46 Br H C1 C1 -CH -C11=C1{
47 Br 11 Cl Cl ( 3)2 48 Br 11 Cl Cl -CH2-CH=CC12 49 ~r C1 C1 Cl -C}1-CH
}3r Cl Cl C1 -C112-C11=C112 15 51 13r Cl C1 Cl C(C}13)2 52 Br Cl Cl. Cl -C}12-CCl=CC12 53 Cl 11 Br 13r -C11-C11 54 Cl 11 Br 13r -C112-CH=C}12 Cl H Br }3r ( 3)2 56 C1 11 13r Br ~C112-C11=C13r2 57 Cl Br Br 13r 2 3 58 . Cl nr nr 13r -C112-C13r=CBr2 The invention also considers as preferretl weed-killer compounds of Eormula (I) those lis-tetl in the following Table 2.
Table 2 Compounds ~ N < 3 O
3o N. X ~ R1 R2 A_ 3 l. Cl -Cll3 2 3 -C!-12- 2 3 2. C1 -Cll3 2 3 -C112- -C}1(C~3)2 1 3 ~8056 .
.: .
: ; 3. Cl. -C1~3 2 3 -C~ - -c~3 4. Cl -C~1-C113 -C112- -C11(C~13)2
5. Cl -CH3 --CH3 -CH2- -C1-12C~13
6- Cl -C(C~13)3 -C1~3 _C~2_ -C}13 05 7. Br -C(C11) -C~1 -C112- -C113 8. ~l -C(ÇH3)3 -C11 -C112- 2 3 9. Br -C(C~13)3 -CH3 -C~12- 2 3 lO. Cl -C(C~3)3 -C1~2C113 -CH2- -CH3 ~ ll. Br -C(CH3)3 -C~12C~13 -CH2- -CH3 ; 12. Cl -C113 -C1{3 2 2 -CH3 14. Cl -C11 -CH2C113 2 2 -CH3 l5. Cl -C~l3 2 3 -C112~H2- -C1i(C113)2 16. Cl -cll3-C~2C113 -CH2CH2- -CH2-C11=C112 : l5 17. Cl -C113-C11(C11) -CH CH ~ -C113 18. Cl -C113( 3)2 112C~12 2 3 19. Cl -C112C113-C~12C113 . 2 2 -C113 20. C]. -C~13-C~1(C11) -C~1-C11- 2 3 ; 20 21. Cl -C2115-C2~15 -C112- -C1~3 22. Cl -C~13-C21l5 3 3 The ratio between -the con1poun(1s of formul.a (II) (and formula III ? nnd those of formula (I) may vary .in use within fairly wide limits and be included in a wei~ht ratio between l:2 and l:lO0.
For -the practical use of the weed-killer cornposition acçording to the invention in agriculture, the antidotes of formula (II) (and those of formula III) are mixed with the weed-ki]lers of formula (I) and with inert substances and adjuvants in suitable formulae, accordin~ to the technique known~to the expert in the field, to obtain, for example liquid solutions emulsifiable i.n water, water-dispersible pastes, wettable powders and ~ranular mixtures.
- J 1 6~056 In the formulae ready for agricultural use, it is also possible to add other active weed-1~iller compounds with complementary or adjuvant action, forming part of the S-tri-azine group (e.g. Atrazine* Si111azine~* Cyanazine*etc.), a 05 Thiolcarbamate (e.g. 13ut:ilate*, EPTC, Vernolate* etc.), a substituted urea (e.g. Linuron* ~lethaben7tia7uron* etc.) or other acetanalides or wee(l-killers.
The use of the composition accordin6 to the invention may take place through distribution with conventional ma-cllines before maize planting, possibly followed by lightincorporation to the soil and by planting (pre-seeding treatment incorporated), or may be effected after planting, but beÇore emergency of the cultivation (pre-emergency treatment), or even after said emergency but always on lS infested grass in the first stages of development (post-e-mergency treatment).
It is possible to distribute, according to the type of weecl-killer used and the relevant antidote, from 0.25 to lO
Kg/11a of total active substances.
The Eollowing examples illustrate the invention more fully without limiting tlle same.
Example of formu]ation - n. 1 .
The following compounds are agitated in a mixer for liquids:
- 2-chlorine-N-(ethoximetllyl)-2'-methyl-6'-ethyl-acetanilide (compound l of formula I) 40.0 Kg.
- N,N-di-n-propyl-dichloroacetamide (compound ll of formula II) lO.O Kg.
- SOIT~1*999 1) l.5 Kg.
30 - SOITEM*lOl l) 4.0 KF.
- Monochlorobenzene 44.5 Kg.
lOO.O Kg.
l) Emulsifiers of the company SOITEM S.p.A. - Milan.
* Trade Mark _ 7 ~'` .
1 3 6~056 Exampl e of f ormul at i on - n . 2 The following are mixed~ ;n a rnixer for liquids:
- 2-chlorine-N-(etllox.imetllyl)-2'-niethyl-6'-ethyl-acetan.i.lide ( Compound 1 of formula I ) 40 . O Kg.
O 5 - 2, 2-climethyl-3-dichloroacetyl-oxazolidine ( compound 16 of formul a II ) 5 . O Kg.
- SOITEM 999 1 ) 2 . O Kg.
- SOITEM 101 1 ) 3.0 Kg.
- Monochlorobenzene 50 O K~-100.0 Kg.
1 ) Emulsifiers of the company SOITEM S.p.A. Milan.
Example of formulation - n. 3 The following components are agi tated in a mixer for l;quids:
- 2 chlorine-N- ( ethoximethyl ) - 2 ' -methyl-6 ' -ethyl-acetanilide (compoun(l of Eormula I, n. 1 tahle 2)40.0 Kg.
- N-ethyl-N-(3,3-d.i.chloroal:l.yl)-~l:i.cllloro-acetamide (eompound of formllla III, n. 2~ table 1 ) 8.o Kg.
2 O - SOITEM 999 1 ) 1. 4 Kg.
- SOITEM 101 1 ) 3 . 7 Kg.
- Monochlorobenzene , 45 . 9 K~-100 . O Kg.
1 ) Emulsifiers of tl~e company SOITEM S.p.A. - Milan.
A liquid emulsifiable in wa-ter is obtained ready for spraying use.
Example_of formulation - n. 4 In a mixer for granular eompounds, first insert 24-48 mesh granular sepiolite to absorb the aeti ve suhstanees aeeording to -the following formula:
- 2-chlorine-N-(ethoximethyl )-2 ' -6 ' -ethylaeetanilide (compound 1 of formula I, tahle 1 ) 10 Kg.
13~'gO5~
- N-allyl N-(3 3-dichl.oroallyl)-dichloroacetamide . . (compound 27 of formula III table 2) 2 K~.
;i - Sepiolite - as many as suffici.ent to reach 100 Kg.
. A granular compound is obtai.ned ready for di.stribution 5 on the fields.
~xample_of applicat;on I
Aqueous emul.si.ons of weed-killer compositions accord-ing to the inventi.on are sprayed on 10 cm. diameter pots containing a sandy so;~ thcn ma.ize seeds Oe the Lampec3llsa variety and seeds of tlie Echinochloa crus g~alli are sowed in these pots.
Both seeds arc covered with 1 cm. of soil and the pots ke~t in a rcenhouse at 15-25C watering twice weekly.
After 30 days the resu.lts in Table 3 are observed; the effects of phytotoxicity on the maize or weecly grass are shown in scale 1-9 where:
1 = healtlly pl.ants 9 = destroyed plants 2 - 8 = intermecliate degrees of phytotoxic:ity Table 3 Phytotoxicity on `malze and on Echinochl Oe convcnt:i.onal. weed-lciller conipos;.t:i.ons witllollt ant;dotes or respecti.vel.y accorcling to the invent;on contain.ing : .
weed-kill.er compounds of formul.a (I) - Tab].e 2 - with or .25 wi.thout substances of formula (II) (and of formula III) -Tabl.e 1 - wi.th antidotic effect on the phytotoxicity of malze observed 30 days after use in pre-seeding oE the -Inalze.
. Compounds (I) Compounds (II) Phytotoxi.city 1-9 3 No. and doses/~la No. and doses~lla on maize on Echinochloa N. 1 2 Kg. +N.11 0.5 Kg. 0 9 N. 1 2 Kg. +N.16 0.3 Kg. 0 : 9 , :
:`
-N. 4 3 K~. +N.19 0.4 Kg. 0 9 N. 6 2 Kg. +N.20 0.2~K6. 0 9 N. 7 3 Kg. -~N.13 o.6 Kg. 0 9 N. 12 3 K6. +N.15 0.4 Kg. 0 9 05 N. 13 2IC6. ~N. 8 0.5 Kg. 0 9 N. 1 2 K~. - 5 9 N. 4 3 K~r. - 7 9 . 6 2 Kg. - 7 9 ~: N. 7 3 Kg. _ 6 9 10N. 12 2 Kg. - 6 9 N. 13 2 Kg. - 6 . 9 It is observed how the compositions with added anti-dote according to the invention are no-t phytotoxic for the maize and preserve full effect:i.vene.ss aga:inst the Echino-chloa crus ~al.l:i, while thc same weed-killer compositions, without added antidotes, are al]. h;.~hly phytotoxic for the ma.ize.
F.xample of appl.ication II
~queous ~mllls:ions of weed-lcil.ler compositions accord-:in~ to the .invellt:i.orl are sprayecl on 10 cm. d.iameter pots containin~ a san(ly so:i:l, therl ma.ize seeds of the Lampedusa vari.ety an~l seeds of the weed Echinochloa crus galli are sowed ln these pots.
: l30th seecls are then covered with 1 cm. of soil and the 25 pots kept in a greenl1ouse at 15-24C, watering tw:ice weekly.
~fter 30 days the results in Table 4 are obta:ined; the effect of phytotoxici.ty on the ma~ze or weedy ~rass is shown in scale 1-9 where:
1 = healthy plants 3 9 = des-troyed plants 2 - 8 = intermedi.ate degrees oÇ phytotoxicity Tabl.e 4 Phytotoxicity on maize and on Echinochloa crus galli I ~ B~056 :
of weed-killer compositions without antido-te or, respective-ly, according to the invention, with antidotes containingr weed-1ciller compositions of formula (I) - l`able 2 - with or without antidotes of formula (III) - Table l -, observed 30 5 days after use in pre-seeding.
Compounc1s (I) Compounds (III) Phytotoxic:Lty 1-9 No. and doses~1-la_ No. and doses/11a on maize on Echinochloa c.g.
N. l 2 K~.~N.24 0.4 ~g. 0 9 ~; N . 4 2 Kg.~N-53 0.4 K~. O 9 lO`N. 6 2 K~.-+N.27 0.4 Kg. 0 9 N. 7 2 Kg.~N.28 0.4 Kg. 0 9 N.12 2 Kg.+N.31 0.4 Kg.~ 0 9 N.13 2 ~6.+N-34 0.4 Kg. 0 9 N. l 2 Kg. - 6 9 ; 15N 4 2 K~. - 5 9 N. 6 2 Kg. - 7 9 N. 7 2 K~. - 4 (~
N.12 2 K~. - 6 9 N.l3 2 K~. - 4 9 20 Xt is observetl how the compositions according to the inve~ntion are not phytotox:ic f`or the maize and preserve Eull effect:iveness against -the Echinoch]oa crus ~alli, while the same weed-1ciller compositions, without -the an-ti-dotes, are all hig111y pl1ytotoxic -for the nnaize.
25 Example of applica-tion III
Aqueous em1llsions of weed-killer composit:ions accord-in~ to the invention are sprayed on lO cm. d:iameter pots containin~ a sandy soil, then sorghum seeds of the Gran Sasso variety and seeds of the weed Ech_nochloa crus galli 3 are planted in these pots.
Both seeds are covered with l cm. of soil and the~pots kept in a greenhousc at 15-25C and watered twice weekly.
.
- ~J68056 ~ fter 30 days the results in Tab]e 5 are observed; the effect of phy-totoxity on-the sorghum and weedy grass is shown in scale 1-9 where:
1 = healthy p].Ants 05 9 = clestroyed p]ants 2 - 8 = intermedi.ate degrees of pl1ytotoxicity : Table 5 Phytotoxicity on sorghum and Echi ochloa crus gall.i of conventional weed-killer composit.;.ons without antidotes or, respectively, according to the invention, with antidotes containin~ weed-ki.ller compositions of formula (I) - Table ~ 2 - with or without antidotes of formula (II) or formula .~ (III) - Table 1 -, observed 30 days after use in pre-seed-.ing of the sorghultl.
Compounds (I) Compounds (II) Compounds (III) Pllytotoxicity 1-9 N. and doses/lla N. an(ldoses1l!a N. and dose~l-la on sor~hum on Echin.
N. 1 2 K~r. N.16 0.5 Kg. - 0 9 ` N. 1 2 Kg. - N.27 0.5 Kg. 0 9 ~ N.21 3 K6r. N.16 -5 K6- - 0 9 20 N.21 3 ~g. - N.27 0.5 Kg. 0 9 N.22 3 Kg: N.20 0.5 Kg. - 0 9 N.22 3 Kg. _ N.24 0.5 Kg. 0 9 N. 1 2 Kg. - - 8 9 N.21 3 Kg - - 7 9 N.22 3 Kg. - - 7 9 It is ohserved how the composi-tions w;.th antidote according to the invention are not phytotoxic for the sorghum and preserve full effectiveness agai.nst the Echino-chloa crus galli., while the same weed-killers, without the add:ition of antidotes, are all highly phytotoxic for the s orghum .
For -the practical use of the weed-killer cornposition acçording to the invention in agriculture, the antidotes of formula (II) (and those of formula III) are mixed with the weed-ki]lers of formula (I) and with inert substances and adjuvants in suitable formulae, accordin~ to the technique known~to the expert in the field, to obtain, for example liquid solutions emulsifiable i.n water, water-dispersible pastes, wettable powders and ~ranular mixtures.
- J 1 6~056 In the formulae ready for agricultural use, it is also possible to add other active weed-1~iller compounds with complementary or adjuvant action, forming part of the S-tri-azine group (e.g. Atrazine* Si111azine~* Cyanazine*etc.), a 05 Thiolcarbamate (e.g. 13ut:ilate*, EPTC, Vernolate* etc.), a substituted urea (e.g. Linuron* ~lethaben7tia7uron* etc.) or other acetanalides or wee(l-killers.
The use of the composition accordin6 to the invention may take place through distribution with conventional ma-cllines before maize planting, possibly followed by lightincorporation to the soil and by planting (pre-seeding treatment incorporated), or may be effected after planting, but beÇore emergency of the cultivation (pre-emergency treatment), or even after said emergency but always on lS infested grass in the first stages of development (post-e-mergency treatment).
It is possible to distribute, according to the type of weecl-killer used and the relevant antidote, from 0.25 to lO
Kg/11a of total active substances.
The Eollowing examples illustrate the invention more fully without limiting tlle same.
Example of formu]ation - n. 1 .
The following compounds are agitated in a mixer for liquids:
- 2-chlorine-N-(ethoximetllyl)-2'-methyl-6'-ethyl-acetanilide (compound l of formula I) 40.0 Kg.
- N,N-di-n-propyl-dichloroacetamide (compound ll of formula II) lO.O Kg.
- SOIT~1*999 1) l.5 Kg.
30 - SOITEM*lOl l) 4.0 KF.
- Monochlorobenzene 44.5 Kg.
lOO.O Kg.
l) Emulsifiers of the company SOITEM S.p.A. - Milan.
* Trade Mark _ 7 ~'` .
1 3 6~056 Exampl e of f ormul at i on - n . 2 The following are mixed~ ;n a rnixer for liquids:
- 2-chlorine-N-(etllox.imetllyl)-2'-niethyl-6'-ethyl-acetan.i.lide ( Compound 1 of formula I ) 40 . O Kg.
O 5 - 2, 2-climethyl-3-dichloroacetyl-oxazolidine ( compound 16 of formul a II ) 5 . O Kg.
- SOITEM 999 1 ) 2 . O Kg.
- SOITEM 101 1 ) 3.0 Kg.
- Monochlorobenzene 50 O K~-100.0 Kg.
1 ) Emulsifiers of the company SOITEM S.p.A. Milan.
Example of formulation - n. 3 The following components are agi tated in a mixer for l;quids:
- 2 chlorine-N- ( ethoximethyl ) - 2 ' -methyl-6 ' -ethyl-acetanilide (compoun(l of Eormula I, n. 1 tahle 2)40.0 Kg.
- N-ethyl-N-(3,3-d.i.chloroal:l.yl)-~l:i.cllloro-acetamide (eompound of formllla III, n. 2~ table 1 ) 8.o Kg.
2 O - SOITEM 999 1 ) 1. 4 Kg.
- SOITEM 101 1 ) 3 . 7 Kg.
- Monochlorobenzene , 45 . 9 K~-100 . O Kg.
1 ) Emulsifiers of tl~e company SOITEM S.p.A. - Milan.
A liquid emulsifiable in wa-ter is obtained ready for spraying use.
Example_of formulation - n. 4 In a mixer for granular eompounds, first insert 24-48 mesh granular sepiolite to absorb the aeti ve suhstanees aeeording to -the following formula:
- 2-chlorine-N-(ethoximethyl )-2 ' -6 ' -ethylaeetanilide (compound 1 of formula I, tahle 1 ) 10 Kg.
13~'gO5~
- N-allyl N-(3 3-dichl.oroallyl)-dichloroacetamide . . (compound 27 of formula III table 2) 2 K~.
;i - Sepiolite - as many as suffici.ent to reach 100 Kg.
. A granular compound is obtai.ned ready for di.stribution 5 on the fields.
~xample_of applicat;on I
Aqueous emul.si.ons of weed-killer compositions accord-ing to the inventi.on are sprayed on 10 cm. diameter pots containing a sandy so;~ thcn ma.ize seeds Oe the Lampec3llsa variety and seeds of tlie Echinochloa crus g~alli are sowed in these pots.
Both seeds arc covered with 1 cm. of soil and the pots ke~t in a rcenhouse at 15-25C watering twice weekly.
After 30 days the resu.lts in Table 3 are observed; the effects of phytotoxicity on the maize or weecly grass are shown in scale 1-9 where:
1 = healtlly pl.ants 9 = destroyed plants 2 - 8 = intermecliate degrees of phytotoxic:ity Table 3 Phytotoxicity on `malze and on Echinochl Oe convcnt:i.onal. weed-lciller conipos;.t:i.ons witllollt ant;dotes or respecti.vel.y accorcling to the invent;on contain.ing : .
weed-kill.er compounds of formul.a (I) - Tab].e 2 - with or .25 wi.thout substances of formula (II) (and of formula III) -Tabl.e 1 - wi.th antidotic effect on the phytotoxicity of malze observed 30 days after use in pre-seeding oE the -Inalze.
. Compounds (I) Compounds (II) Phytotoxi.city 1-9 3 No. and doses/~la No. and doses~lla on maize on Echinochloa N. 1 2 Kg. +N.11 0.5 Kg. 0 9 N. 1 2 Kg. +N.16 0.3 Kg. 0 : 9 , :
:`
-N. 4 3 K~. +N.19 0.4 Kg. 0 9 N. 6 2 Kg. +N.20 0.2~K6. 0 9 N. 7 3 Kg. -~N.13 o.6 Kg. 0 9 N. 12 3 K6. +N.15 0.4 Kg. 0 9 05 N. 13 2IC6. ~N. 8 0.5 Kg. 0 9 N. 1 2 K~. - 5 9 N. 4 3 K~r. - 7 9 . 6 2 Kg. - 7 9 ~: N. 7 3 Kg. _ 6 9 10N. 12 2 Kg. - 6 9 N. 13 2 Kg. - 6 . 9 It is observed how the compositions with added anti-dote according to the invention are no-t phytotoxic for the maize and preserve full effect:i.vene.ss aga:inst the Echino-chloa crus ~al.l:i, while thc same weed-killer compositions, without added antidotes, are al]. h;.~hly phytotoxic for the ma.ize.
F.xample of appl.ication II
~queous ~mllls:ions of weed-lcil.ler compositions accord-:in~ to the .invellt:i.orl are sprayecl on 10 cm. d.iameter pots containin~ a san(ly so:i:l, therl ma.ize seeds of the Lampedusa vari.ety an~l seeds of the weed Echinochloa crus galli are sowed ln these pots.
: l30th seecls are then covered with 1 cm. of soil and the 25 pots kept in a greenl1ouse at 15-24C, watering tw:ice weekly.
~fter 30 days the results in Table 4 are obta:ined; the effect of phytotoxici.ty on the ma~ze or weedy ~rass is shown in scale 1-9 where:
1 = healthy plants 3 9 = des-troyed plants 2 - 8 = intermedi.ate degrees oÇ phytotoxicity Tabl.e 4 Phytotoxicity on maize and on Echinochloa crus galli I ~ B~056 :
of weed-killer compositions without antido-te or, respective-ly, according to the invention, with antidotes containingr weed-1ciller compositions of formula (I) - l`able 2 - with or without antidotes of formula (III) - Table l -, observed 30 5 days after use in pre-seeding.
Compounc1s (I) Compounds (III) Phytotoxic:Lty 1-9 No. and doses~1-la_ No. and doses/11a on maize on Echinochloa c.g.
N. l 2 K~.~N.24 0.4 ~g. 0 9 ~; N . 4 2 Kg.~N-53 0.4 K~. O 9 lO`N. 6 2 K~.-+N.27 0.4 Kg. 0 9 N. 7 2 Kg.~N.28 0.4 Kg. 0 9 N.12 2 Kg.+N.31 0.4 Kg.~ 0 9 N.13 2 ~6.+N-34 0.4 Kg. 0 9 N. l 2 Kg. - 6 9 ; 15N 4 2 K~. - 5 9 N. 6 2 Kg. - 7 9 N. 7 2 K~. - 4 (~
N.12 2 K~. - 6 9 N.l3 2 K~. - 4 9 20 Xt is observetl how the compositions according to the inve~ntion are not phytotox:ic f`or the maize and preserve Eull effect:iveness against -the Echinoch]oa crus ~alli, while the same weed-1ciller compositions, without -the an-ti-dotes, are all hig111y pl1ytotoxic -for the nnaize.
25 Example of applica-tion III
Aqueous em1llsions of weed-killer composit:ions accord-in~ to the invention are sprayed on lO cm. d:iameter pots containin~ a sandy soil, then sorghum seeds of the Gran Sasso variety and seeds of the weed Ech_nochloa crus galli 3 are planted in these pots.
Both seeds are covered with l cm. of soil and the~pots kept in a greenhousc at 15-25C and watered twice weekly.
.
- ~J68056 ~ fter 30 days the results in Tab]e 5 are observed; the effect of phy-totoxity on-the sorghum and weedy grass is shown in scale 1-9 where:
1 = healthy p].Ants 05 9 = clestroyed p]ants 2 - 8 = intermedi.ate degrees of pl1ytotoxicity : Table 5 Phytotoxicity on sorghum and Echi ochloa crus gall.i of conventional weed-killer composit.;.ons without antidotes or, respectively, according to the invention, with antidotes containin~ weed-ki.ller compositions of formula (I) - Table ~ 2 - with or without antidotes of formula (II) or formula .~ (III) - Table 1 -, observed 30 days after use in pre-seed-.ing of the sorghultl.
Compounds (I) Compounds (II) Compounds (III) Pllytotoxicity 1-9 N. and doses/lla N. an(ldoses1l!a N. and dose~l-la on sor~hum on Echin.
N. 1 2 K~r. N.16 0.5 Kg. - 0 9 ` N. 1 2 Kg. - N.27 0.5 Kg. 0 9 ~ N.21 3 K6r. N.16 -5 K6- - 0 9 20 N.21 3 ~g. - N.27 0.5 Kg. 0 9 N.22 3 Kg: N.20 0.5 Kg. - 0 9 N.22 3 Kg. _ N.24 0.5 Kg. 0 9 N. 1 2 Kg. - - 8 9 N.21 3 Kg - - 7 9 N.22 3 Kg. - - 7 9 It is ohserved how the composi-tions w;.th antidote according to the invention are not phytotoxic for the sorghum and preserve full effectiveness agai.nst the Echino-chloa crus galli., while the same weed-killers, without the add:ition of antidotes, are all highly phytotoxic for the s orghum .
Claims (12)
1. Selective weed-killer composition for maize and sorghum comprising (a) a weed-killer compound with the formula:
(I) where R1 and R2 are alkyl with 1-4 atoms of carbon; A is -CH2-; -CH2-CH2-; ; R3 is alkyl with 2-4 carbon atoms and X is chlorine or bromine and (b) an antidote of the formula:
(II) where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylaniline; R2 is hydrogen, alkyl, haloalkyl, haloalkenyl, alkinyl, phenyl, the alipha-tic radicals having 1-4 carbon atoms and the halogens being chlorine or bromine; or R1 and R2 may form a ring struc-ture selected from piperidyl, alkylpiperidyl, morpholyl, alkylmorpholyl, hexamethylenimine, oxazolidine, 2,2-dimethyl-oxazolidine, 5- alkoxymethyl-2,2-dimethyl oxa-zolidine.
(I) where R1 and R2 are alkyl with 1-4 atoms of carbon; A is -CH2-; -CH2-CH2-; ; R3 is alkyl with 2-4 carbon atoms and X is chlorine or bromine and (b) an antidote of the formula:
(II) where R is haloalkyl; R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, 2,6-dialkylaniline; R2 is hydrogen, alkyl, haloalkyl, haloalkenyl, alkinyl, phenyl, the alipha-tic radicals having 1-4 carbon atoms and the halogens being chlorine or bromine; or R1 and R2 may form a ring struc-ture selected from piperidyl, alkylpiperidyl, morpholyl, alkylmorpholyl, hexamethylenimine, oxazolidine, 2,2-dimethyl-oxazolidine, 5- alkoxymethyl-2,2-dimethyl oxa-zolidine.
2. Composition as claimed in claim 1, where the compound of formula (I) is 2-chloro-N-(ethoxymethyl)-2'-methyl-6'-ethyl-acetanilide.
3. Composition as claimed in claim 1, where the compound of formula (I) is 2-chloro-N-(isopropoxymethyl)-2',6'-dimethyl-acetanilide.
4. Composition as claimed in claim 1, where the compound of formula (I) is 2-bromo-N-(methoxymethyl)-2'-t-butyl-6'-methyl-acetanilide.
5. Composition as claimed in claim 1, where the compound of formula (II) is N-ethyl-N-(3,3-dichloroallyl)-dichloroacetamide.
6. Composition as claimed in claim 1, where the compound of formula (II) is N-allyl-N(3,3-dichloroallyl)-dichloroacetamide.
7. Composition as claimed in claim 1, where the compound of formula (II) is N,N-di-n-propyl-dichloroaceta-mide.
8. Composition as claimed in claim 1, where the compound of formula (II) is 2,2 dimethyl-3-dichloroacetyl-oxazolidine.
9. Composition as claimed in claim 1, where the compound of formula (II) is 2,2-dimethyl-3-dichloroacetyl-5-methoxymethyl-oxazolidine.
10. Composition as claimed in claim 1, where the compound of formula (II) is N-piperidyl-dichloroacetamide.
11. Composition as claimed in claim 1, in which the weight ratio between compounds of formula (I) and for-mula (II) is between 1:2 and 1 100.
12. Process for weed-killing in fields of maize that comprises applying a composition claimed in any one of claims 1 to 3, by distributing 0.25 to 10 kg./Ha of total active substances in pre-seeding, pre-emergency or post-emergency stage.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24566A/81 | 1981-10-20 | ||
| IT24566/81A IT1168041B (en) | 1981-10-20 | 1981-10-20 | Selective herbicide compsn. for maize and sorghum |
| IT21022/82A IT1190795B (en) | 1982-04-30 | 1982-04-30 | Selective herbicide compsn. for maize and sorghum |
| IT21022A/82 | 1982-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1168056A true CA1168056A (en) | 1984-05-29 |
Family
ID=26327733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413740A Expired CA1168056A (en) | 1981-10-20 | 1982-10-19 | Weed-killer composition containing amides as antidotes for alpha-halo-acetanilides |
Country Status (3)
| Country | Link |
|---|---|
| BR (1) | BR8206082A (en) |
| CA (1) | CA1168056A (en) |
| FR (1) | FR2514611A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762548A (en) * | 1985-08-12 | 1988-08-09 | Stauffer Chemical Co. | Herbicide compositions of extended soil life |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ222993A (en) * | 1986-12-22 | 1989-09-27 | Stauffer Agricultural Chemical | Herbicidal compositions containing an acyl substituted oxazolidone antidote and two active herbicides |
| EE9500018A (en) | 1994-06-03 | 1995-12-15 | Ciba-Geigy Ag | Selective herbicide and method of application |
| FR2762475B1 (en) * | 1997-04-25 | 1999-07-16 | Nitrokemia Rt | HERBICIDE COMPOSITIONS BASED ON CHLOROACETAMIDE AND 1,3,5-TRIAZINE AND THEIR USE |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4033756A (en) * | 1971-09-17 | 1977-07-05 | Gulf Research & Development Company | Dichloroacetamide treated rice seeds |
| US4021224A (en) * | 1971-12-09 | 1977-05-03 | Stauffer Chemical Company | Herbicide compositions |
| US4243811A (en) * | 1972-10-13 | 1981-01-06 | Stauffer Chemical Company | 2,2,4-Trimethyl-4-hydroxymethyl-3-dichloroacetyl oxazolidine |
| CH574207A5 (en) * | 1973-01-25 | 1976-04-15 | Ciba Geigy Ag | |
| IT1079199B (en) * | 1976-10-29 | 1985-05-08 | Montedison Spa | ANTIDOTES, OF THE CLASS OF DICHLOROACETAMIDES PARTICULARLY ACTIVE IN PROTECTING MAIZE FROM TOXIC ACTION EXERCISED BY GLYCINE ESTERS N, N SUBSTITUTED HERBICIDE AND HERBICIDE ASSOCIATION FOR MAIZE CULTURES |
| IT1114195B (en) * | 1977-12-23 | 1986-01-27 | Montedison Spa | TWO DICHLOROACETAMIDE ANTIDUCTS FOR NON-SELECTIVE HERBICIDES PARTICULARLY ACTIVE TO PROTECT THE MAIZE FROM TOXIC ACTION EXERCISED BY GLYCIN ESTERS N, N HERBICIDES REPLACED |
| BE874361A (en) * | 1978-02-06 | 1979-06-18 | Nitrokemia Ipartelepek | SELECTIVE HERBICIDE COMPOSITION |
-
1982
- 1982-10-19 BR BR8206082A patent/BR8206082A/en unknown
- 1982-10-19 CA CA000413740A patent/CA1168056A/en not_active Expired
- 1982-10-20 FR FR8217559A patent/FR2514611A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762548A (en) * | 1985-08-12 | 1988-08-09 | Stauffer Chemical Co. | Herbicide compositions of extended soil life |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8206082A (en) | 1983-09-13 |
| FR2514611A1 (en) | 1983-04-22 |
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| JPS6141490B2 (en) | ||
| TH32605A (en) | Mixture with herbicide properties |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |